chore: Helix Bridge 3.18.0 changelog.

(cherry picked from commit 6105f32c75)

.github/ISSUE_TEMPLATE/general-issue-template.md

@@ -1,41 +0,0 @@
----
-name: General issue template
-about: Template for detailed report of issues
-title: ''
-labels: ''
-assignees: ''
-
----
-
-Issue tracker is ONLY used for reporting bugs with technical details. "It doesn't work" or new features should be discussed with our customer support. Please use bug report function in Bridge or contact bridge@protonmail.ch.
-<!--- Provide a general summary of the issue in the Title above -->
-
-## Expected Behavior
-<!--- Tell us what should happen -->
-
-## Current Behavior
-<!--- Tell us what happens instead of the expected behavior -->
-
-## Possible Solution
-<!--- Not obligatory, but suggest a fix/reason for the bug, -->
-
-## Steps to Reproduce
-<!--- Provide a link to a live example, or an unambiguous set of steps to -->
-<!--- reproduce this bug. Include code to reproduce, if relevant -->
-1.
-2.
-3.
-4.
-
-## Version Information
-<!--- Which version of the app(s) were you using when you experienced this issue? -->
-
-## Context (Environment)
-<!--- How has this issue affected you? What are you trying to accomplish? -->
-<!--- Providing context helps us come up with a solution that is most useful in the real world -->
-
-## Detailed Description
-<!--- Provide a detailed description of the change or addition you are proposing -->
-
-## Possible Implementation
-<!--- Not obligatory, but suggest an idea for implementing addition or change -->

.gitignore

@@ -7,6 +7,7 @@
 *~
 .idea
 .vscode
+.vs
 
 # Test files
 godog.test
@@ -35,9 +36,15 @@ cmd/Import-Export/deploy
 proton-bridge
 cmd/Desktop-Bridge/*.exe
 cmd/launcher/*.exe
+bin/
+obj/
 
 # Jetbrains (CLion, Golang) cmake build dirs
 cmake-build-*/
 
 # Doxygen doc files
 _doc/
+
+# gRPC auto-generated C++ source files
+*.pb.cc
+*.pb.h

.gitlab-ci.yml

@@ -16,221 +16,35 @@
 # along with ProtonMail Bridge.  If not, see <https://www.gnu.org/licenses/>.
 
 ---
-image: harbor.protontech.ch/docker.io/library/golang:1.18
+default:
+  tags:
+    - shared-small
 
 variables:
   GOPRIVATE: gitlab.protontech.ch
   GOMAXPROCS: $(( ${CI_TAG_CPU} / 2 ))
 
 before_script:
-  - apt update && apt-get -y install libsecret-1-dev
-  - git config --global url.https://gitlab-ci-token:${CI_JOB_TOKEN}@${CI_SERVER_HOST}.insteadOf https://${CI_SERVER_HOST}
+  - |
+    if [ "$CI_JOB_NAME" != "grype-scan-code-dependencies" ]; then
+      apt update && apt-get -y install libsecret-1-dev
+      git config --global url.https://gitlab-ci-token:${CI_JOB_TOKEN}@${CI_SERVER_HOST}.insteadOf https://${CI_SERVER_HOST}
+    fi
 
 stages:
+  - analyse
   - test
+  - report
   - build
 
-.rules-branch-and-MR-always:
-  rules:
-    - if: $CI_COMMIT_BRANCH ||  $CI_PIPELINE_SOURCE == "merge_request_event"
-      when: always
-      allow_failure: false
-    - when: never
+include:
+  - local: ci/setup.yml
+  - local: ci/rules.yml
+  - local: ci/env.yml
+  - local: ci/test.yml
+  - local: ci/report.yml
+  - local: ci/build.yml
+  - component: gitlab.protontech.ch/proton/devops/cicd-components/kits/devsecops/go@~latest
+    inputs:
+      stage: analyse
 
-.rules-branch-and-MR-manual:
-  rules:
-    - if: $CI_COMMIT_BRANCH ||  $CI_PIPELINE_SOURCE == "merge_request_event"
-      when: manual
-      allow_failure: true
-    - when: never
-
-.rules-branch-manual-MR-always:
-  rules:
-    - if: $CI_PIPELINE_SOURCE == "merge_request_event"
-      when: always
-      allow_failure: false
-    - if: $CI_COMMIT_BRANCH
-      when: manual
-      allow_failure: true
-    - when: never
-
-# Stage: TEST
-
-lint:
-  stage: test
-  extends:
-    - .rules-branch-and-MR-always
-  script:
-    - make lint
-  tags:
-    - medium
-
-test-linux:
-  stage: test
-  extends:
-    - .rules-branch-manual-MR-always
-  script:
-    - make test
-  tags:
-    - medium
-
-test-linux-race:
-  stage: test
-  extends:
-    - .rules-branch-and-MR-manual
-  script:
-    - make test-race
-  tags:
-    - medium
-
-test-integration:
-  stage: test
-  extends:
-    - .rules-branch-manual-MR-always
-  script:
-    - make test-integration
-  tags:
-    - large
-
-test-integration-race:
-  stage: test
-  extends:
-    - .rules-branch-and-MR-manual
-  script:
-    - make test-integration-race
-  tags:
-    - large
-
-dependency-updates:
-  stage: test
-  script:
-    - make updates
-
-# Stage: BUILD
-
-.build-base:
-  stage: build
-  needs: ["lint"]
-  rules:
-    # GODT-1833: use `=~ /qa/` after mac and windows runners are fixed
-    - if: $CI_JOB_NAME =~ /build-linux-qa/  && $CI_PIPELINE_SOURCE == "merge_request_event"
-      when: always
-      allow_failure: false
-    - if: $CI_COMMIT_BRANCH || $CI_PIPELINE_SOURCE == "merge_request_event"
-      when: manual
-      allow_failure: true
-    - when: never
-  before_script:
-    - mkdir -p .cache/bin
-    - export PATH=$(pwd)/.cache/bin:$PATH
-    - export GOPATH="$CI_PROJECT_DIR/.cache"
-    - export PATH=$PATH:$QT6DIR/bin
-    - $(git config --global -l | grep -o 'url.*gitlab.protontech.ch.*insteadof' | xargs -L 1 git config --global --unset &> /dev/null) || echo "nothing to remove"
-    - git config --global url.https://gitlab-ci-token:${CI_JOB_TOKEN}@${CI_SERVER_HOST}.insteadOf https://${CI_SERVER_HOST}
-  script:
-    - make build
-    - git diff && git diff-index --quiet HEAD
-    - make vault-editor
-  artifacts:
-    # Note: The latest artifacts for refs are locked against deletion, and kept
-    # regardless of the expiry time. Introduced in GitLab 13.0 behind a
-    # disabled feature flag, and made the default behavior in GitLab 13.4.
-    expire_in: 1 day
-    when: always
-    paths:
-      - bridge_*.tgz
-      - vault-editor
-  tags:
-    - large
-
-build-linux:
-  extends: .build-base
-  image: gitlab.protontech.ch:4567/go/bridge-internal:qt6
-  variables:
-    VCPKG_DEFAULT_BINARY_CACHE: ${CI_PROJECT_DIR}/.cache
-  cache:
-    key: linux-vcpkg
-    paths:
-      - .cache
-    when: 'always'
-  artifacts:
-    name: "bridge-linux-$CI_COMMIT_SHORT_SHA"
-
-build-linux-qa:
-  extends: build-linux
-  variables:
-    BUILD_TAGS: "build_qa"
-  artifacts:
-    name: "bridge-linux-qa-$CI_COMMIT_SHORT_SHA"
-
-
-.build-darwin-base:
-  extends: .build-base
-  before_script:
-    - export PATH=/usr/local/bin:$PATH
-    - export PATH=/usr/local/opt/git/bin:$PATH
-    - export PATH=/usr/local/opt/make/libexec/gnubin:$PATH
-    - export PATH=/usr/local/opt/go@1.13/bin:$PATH
-    - export PATH=/usr/local/opt/gnu-sed/libexec/gnubin:$PATH
-    - export GOPATH=~/go
-    - export PATH=$GOPATH/bin:$PATH
-    - export CGO_CPPFLAGS='-Wno-error -Wno-nullability-completeness -Wno-expansion-to-defined -Wno-builtin-requires-header'
-    - $(git config --global -l | grep -o 'url.*gitlab.protontech.ch.*insteadof' | xargs -L 1 git config --global --unset &> /dev/null) || echo "nothing to remove"
-    - git config --global url.https://gitlab-ci-token:${CI_JOB_TOKEN}@${CI_SERVER_HOST}.insteadOf https://${CI_SERVER_HOST}
-  script:
-    - go version
-    - make build-nogui
-    - git diff && git diff-index --quiet HEAD
-    - make vault-editor
-  cache: {}
-  tags:
-    - macOS
-
-build-darwin:
-  extends: .build-darwin-base
-  artifacts:
-    name: "bridge-darwin-$CI_COMMIT_SHORT_SHA"
-
-build-darwin-qa:
-  extends: .build-darwin-base
-  variables:
-    BUILD_TAGS: "build_qa"
-  artifacts:
-    name: "bridge-darwin-qa-$CI_COMMIT_SHORT_SHA"
-
-
-.build-windows-base:
-  extends: .build-base
-  before_script:
-    - export GOROOT=/c/Go1.18/
-    - export PATH=$GOROOT/bin:$PATH
-    - export GOARCH=amd64
-    - export GOPATH=~/go18
-    - export GO111MODULE=on
-    - export PATH="${GOPATH}/bin:${PATH}"
-    - export MSYSTEM=
-    - export QT6DIR=/c/grrrQt/6.3.1/msvc2019_64
-    - export PATH=$PATH:${QT6DIR}/bin
-    - export PATH="/c/Program Files/Microsoft Visual Studio/2022/Community/Common7/IDE/CommonExtensions/Microsoft/CMake/CMake/bin:$PATH"
-    - $(git config --global -l | grep -o 'url.*gitlab.protontech.ch.*insteadof' | xargs -L 1 git config --global --unset &> /dev/null) || echo "nothing to remove"
-    - git config --global url.https://gitlab-ci-token:${CI_JOB_TOKEN}@${CI_SERVER_HOST}.insteadOf https://${CI_SERVER_HOST}
-  script:
-    - make build-nogui
-    - git diff && git diff-index --quiet HEAD
-    - make vault-editor
-  tags:
-    - windows-bridge
-
-build-windows:
-  extends: .build-windows-base
-  artifacts:
-    name: "bridge-windows-$CI_COMMIT_SHORT_SHA"
-
-build-windows-qa:
-  extends: .build-windows-base
-  variables:
-    BUILD_TAGS: "build_qa"
-  artifacts:
-    name: "bridge-windows-qa-$CI_COMMIT_SHORT_SHA"
-
-# TODO: PUT BACK ALL THE JOBS! JUST DID THIS FOR NOW TO GET CI WORKING AGAIN...

.gitlab/CODEOWNERS

@@ -0,0 +1 @@
+* @go/bridge-ppl/devs

.golangci.yml

@@ -2,11 +2,12 @@
 run:
   timeout: 10m
   skip-dirs:
-    - pkg/mime
-    - extern
 
 issues:
   exclude-use-default: false
+  exclude-dirs:
+    - pkg/mime
+    - extern
   exclude:
     - Using the variable on range scope `tt` in function literal
     # For now we are missing a lot of comments.
@@ -23,7 +24,6 @@ issues:
     - path: _test\.go
       linters:
         - dupl
-        - funlen
         - gochecknoglobals
         - gochecknoinits
         - gosec
@@ -32,7 +32,14 @@ issues:
     - path: test
       linters:
         - dupl
-        - funlen
+        - gochecknoglobals
+        - gochecknoinits
+        - gosec
+        - goconst
+        - dogsled
+    - path: utils/smtp-send
+      linters:
+        - dupl
         - gochecknoglobals
         - gochecknoinits
         - gosec
@@ -50,21 +57,17 @@ linters:
   disable-all: true
 
   enable:
-    - deadcode          # Finds unused code [fast: true, auto-fix: false]
     - errcheck          # Errcheck is a program for checking for unchecked errors in go programs. These unchecked errors can be critical bugs in some cases [fast: true, auto-fix: false]
     - gosimple          # Linter for Go source code that specializes in simplifying a code [fast: true, auto-fix: false]
     - govet             # Vet examines Go source code and reports suspicious constructs, such as Printf calls whose arguments do not align with the format string [fast: true, auto-fix: false]
     - ineffassign       # Detects when assignments to existing variables are not used [fast: true, auto-fix: false]
     - staticcheck       # Staticcheck is a go vet on steroids, applying a ton of static analysis checks [fast: true, auto-fix: false]
-    - structcheck       # Finds unused struct fields [fast: true, auto-fix: false]
     - typecheck         # Like the front-end of a Go compiler, parses and type-checks Go code [fast: true, auto-fix: false]
     - unused            # Checks Go code for unused constants, variables, functions and types [fast: false, auto-fix: false]
-    - varcheck          # Finds unused global variables and constants [fast: true, auto-fix: false]
     - bodyclose         # checks whether HTTP response body is closed successfully [fast: true, auto-fix: false]
-    - depguard          # Go linter that checks if package imports are in a list of acceptable packages [fast: true, auto-fix: false]
+    #- depguard          # Go linter that checks if package imports are in a list of acceptable packages [fast: true, auto-fix: false]
     - dogsled           # Checks assignments with too many blank identifiers (e.g. x, _, _, _, := f()) [fast: true, auto-fix: false]
     - dupl              # Tool for code clone detection [fast: true, auto-fix: false]
-    - funlen            # Tool for detection of long functions [fast: true, auto-fix: false]
     - gochecknoglobals  # Checks that no globals are present in Go code [fast: true, auto-fix: false]
     - gochecknoinits    # Checks that no init functions are present in Go code [fast: true, auto-fix: false]
     - goconst           # Finds repeated strings that could be replaced by a constant [fast: true, auto-fix: false]
@@ -84,7 +87,7 @@ linters:
     - asciicheck        # Simple linter to check that your code does not contain non-ASCII identifiers [fast: true, auto-fix: false]
     - durationcheck     # check for two durations multiplied together [fast: false, auto-fix: false]
     - exhaustive        # check exhaustiveness of enum switch statements [fast: false, auto-fix: false]
-    - exportloopref     # checks for pointers to enclosing loop variables [fast: false, auto-fix: false]
+    - copyloopvar       # detects places where loop variables are copied.
     - forcetypeassert   # finds forced type assertions [fast: true, auto-fix: false]
     - godot             # Check if comments end in a period [fast: true, auto-fix: true]
     - goheader          # Checks is file header matches to pattern [fast: true, auto-fix: false]
@@ -122,3 +125,8 @@ linters:
     # - testpackage       # linter that makes you use a separate _test package [fast: true, auto-fix: false]
     # - thelper           # thelper detects golang test helpers without t.Helper() call and checks the consistency of test helpers [fast: false, auto-fix: false]
     # - wrapcheck         # Checks that errors returned from external packages are wrapped [fast: false, auto-fix: false]
+
+    # Deprecated:
+    # - structcheck       # Finds unused struct fields [fast: true, auto-fix: false] deprecated (since v1.49.0) due to: The owner seems to have abandoned the linter. Replaced by unused.
+    # - deadcode          # Finds unused code [fast: true, auto-fix: false] deprecated (since v1.49.0) due to: The owner seems to have abandoned the linter. Replaced by unused.
+    # - varcheck          # Finds unused global variables and constants [fast: true, auto-fix: false] deprecated (since v1.49.0) due to: The owner seems to have abandoned the linter. Replaced by unused.

.grype.yaml

@@ -0,0 +1,2 @@
+# Check out for configuration details: https://github.com/anchore/grype?tab=readme-ov-file#configuration
+fail-on-severity: "medium"

BUILDS.md

@@ -3,20 +3,23 @@
 ## Prerequisites
 * 64-bit OS:
     - the go-rfc5322 module cannot currently be compiled for 32-bit OSes
-* Go 1.18
+* Go 1.23.4
 * Bash with basic build utils: make, gcc, sed, find, grep, ...
   - For Windows, it is recommended to use MinGW 64bit shell from [MSYS2](https://www.msys2.org/)
-* GCC (linux), msvc (windows) or Xcode (macOS)
-* Windres (windows)
-* libglvnd and libsecret development files (linux)
+* GCC (Linux), msvc (Windows) or Xcode (macOS)
+* Windres (Windows)
+* libglvnd and libsecret development files (Linux)
+* pkg-config (Linux)
+* cmake, ninja-build and Qt 6.4.3 are required to build the graphical user interface. On Linux, 
+the Mesa OpenGL development files are also needed.
 
 To enable the sending of crash reports using Sentry please set the
-`main.DSNSentry` value with the client key of your sentry project before build.
+`DSN_SENTRY` environment variable with the client key of your sentry project before build.
 Otherwise, the sending of crash reports will be disabled.
 
 ## Build
 In order to build Bridge app with Qt interface we are using
-[Qt 6.3](https://doc.qt.io/qt-6/gettingstarted.html).
+[Qt 6.4.3](https://doc.qt.io/qt-6/gettingstarted.html).
 
 Please note that qmake path must be in your `PATH` to ensure Qt to be found.
 Also, before you start build **on Windows**, please unset the `MSYSTEM` variable

CONTRIBUTING.md

@@ -1,10 +1,78 @@
-# Contribution Policy
+# Contributing guidelines
+
+The following document describes how to contribute to the project. In this context, contribution does not only mean code contribution but also reporting issues, requesting new features, or just asking for help.
+
+## Reporting issues
+
+In case you experience issues while using the application, our request is to contact Proton customer support directly.
+
+The benefits of using Proton customer support are
+
+- Available 24/7/365.
+- Provides priority support based on subscription type.
+- Will escalate the issue to the developers every time it becomes too technical or they do not know the answer to a question.
+- Easier to detect systematic issues by connecting similar reports.
+- Possible to quickly derive frequency of an issue.
+- Can assist you to transfer sensitive information safely to us.
+
+To speed up the communication with customer support, consider the following:
+
+- Whenever is possible, use the in-app bug report feature. It provides an application specific guide compared to using the generic report form on web.
+- Whenever is possible, proactively attach logs to your report. Reporting an issue from the application can help you in that.
+- Check whether your system is officially supported by Proton, including the source of the installer. We cannot provide help when the application is packaged by a third party or when the application is used on systems that we do not prepare to support.
+- If your report is a feature request, see the Feature request section. In case it is an issue related to application security, see the Security vulnerabilities section.
+
+In the past, we used GitHub issue tracker for more technical issues in parallel to Proton customer support, but we run into limitations with this approach:
+
+- Monitoring GitHub issue tracker took development time as it was managed by the development team.
+- It made issue frequency tracking challenging because we did not have a single point of entry for issues.
+- Users were confused what technical issue means, and used the GitHub issue tracker for feature requests, or non-technical discussions.
+- Users sometimes shared sensitive data through the GitHub issue tracker.
+
+For the above reasons, we do not use GitHub issue tracker anymore but ask you to contact our customer support in case you run into a problem.
+
+### Security vulnerabilities
+
+Proton runs a bug bounty program for security vulnerabilities. They differ from normal bug reports in the following ways:
+
+- These reports go directly to our security team.
+- They expect deeper explanation of the issue.
+- Depending on the finding, they may be financially rewarded.
+
+More information about the program can be found [here](https://proton.me/security/bug-bounty).
+
+## Feature requests
+
+What someone considers as a bug is sometimes a feature, and sometimes, a missing feature is considered as a bug. Instead of reporting feature requests as bugs, we setup a UserVoice page to allow our users to share their preferences. UserVoice also makes it possible to vote on other feature requests, making the community preference public.
+
+Our product team frequently monitors UserVoice, and the features listed there are taken into account in our planning.
+
+Examples for UserVoice requests:
+
+- Extending the officially supported environments (e.g., operating systems, clients, or computer architectures).
+- Requesting new features.
+- Integration with non-Proton services.
+
+UserVoice is available [here](https://protonmail.uservoice.com/).
+
+## Asking for help
+
+The best ways to get answer for generic questions or to get help with setting up the system is to interact with our active community on [Reddit](https://reddit.com/r/ProtonMail/) or to contact customer support.
+
+## Code contribution
+
+We are grateful if you can contribute directly with code. In that case there is nothing else to do than to open a pull request.
+
+The following is worthwhile noting
+
+- The project is primarily developed on an internal repository, and the one on GitHub is only a mirror of it. For that reason, the merge request will not be merged on GitHub but added to the project internally. We are keeping the original author in the change set to respect the contribution.
+- The application is used on numerous platforms and by many third party clients. To have higher chance your change to be accepted, consider all supported dependencies.
+- Give detailed description of the issue, preferably with test steps to reproduce the original issue, and to verify the fix. It is even better if you also extend the automated tests.
+
+### Contribution policy
 
 By making a contribution to this project:
 
-1.  I assign any and all copyright related to the contribution to Proton AG;
-2.  I certify that the contribution was created in whole by me;
-3.  I understand and agree that this project and the contribution are public
-    and that a record of the contribution (including all personal information I
-    submit with it) is maintained indefinitely and may be redistributed with
-    this project or the open source license(s) involved.
+1. You assign any and all copyright related to the contribution to Proton AG;
+2. You certify that the contribution was created in whole by you;
+3. You understand and agree that this project and the contribution are public and that a record of the contribution (including all personal information you submit with it) is maintained indefinitely and may be redistributed with this project or the open source license(s) involved.

COPYING_NOTES.md

@@ -26,7 +26,6 @@ Proton Mail Bridge includes the following 3rd party software:
 * [gluon](https://github.com/ProtonMail/gluon) available under [license](https://github.com/ProtonMail/gluon/blob/master/LICENSE) 
 * [go-autostart](https://github.com/ProtonMail/go-autostart) available under [license](https://github.com/ProtonMail/go-autostart/blob/master/LICENSE) 
 * [go-proton-api](https://github.com/ProtonMail/go-proton-api) available under [license](https://github.com/ProtonMail/go-proton-api/blob/master/LICENSE) 
-* [go-rfc5322](https://github.com/ProtonMail/go-rfc5322) available under [license](https://github.com/ProtonMail/go-rfc5322/blob/master/LICENSE) 
 * [gopenpgp](https://github.com/ProtonMail/gopenpgp/v2) available under [license](https://github.com/ProtonMail/gopenpgp/v2/blob/master/LICENSE) 
 * [goquery](https://github.com/PuerkitoBio/goquery) available under [license](https://github.com/PuerkitoBio/goquery/blob/master/LICENSE) 
 * [ishell](https://github.com/abiosoft/ishell) available under [license](https://github.com/abiosoft/ishell/blob/master/LICENSE) 
@@ -41,43 +40,46 @@ Proton Mail Bridge includes the following 3rd party software:
 * [go-message](https://github.com/emersion/go-message) available under [license](https://github.com/emersion/go-message/blob/master/LICENSE) 
 * [go-sasl](https://github.com/emersion/go-sasl) available under [license](https://github.com/emersion/go-sasl/blob/master/LICENSE) 
 * [go-smtp](https://github.com/emersion/go-smtp) available under [license](https://github.com/emersion/go-smtp/blob/master/LICENSE) 
+* [go-vcard](https://github.com/emersion/go-vcard) available under [license](https://github.com/emersion/go-vcard/blob/master/LICENSE) 
 * [color](https://github.com/fatih/color) available under [license](https://github.com/fatih/color/blob/master/LICENSE) 
 * [sentry-go](https://github.com/getsentry/sentry-go) available under [license](https://github.com/getsentry/sentry-go/blob/master/LICENSE) 
 * [resty](https://github.com/go-resty/resty/v2) available under [license](https://github.com/go-resty/resty/v2/blob/master/LICENSE) 
-* [go-json](https://github.com/goccy/go-json) available under [license](https://github.com/goccy/go-json/blob/master/LICENSE) 
 * [dbus](https://github.com/godbus/dbus) available under [license](https://github.com/godbus/dbus/blob/master/LICENSE) 
 * [mock](https://github.com/golang/mock) available under [license](https://github.com/golang/mock/blob/master/LICENSE) 
 * [go-cmp](https://github.com/google/go-cmp) available under [license](https://github.com/google/go-cmp/blob/master/LICENSE) 
 * [uuid](https://github.com/google/uuid) available under [license](https://github.com/google/uuid/blob/master/LICENSE) 
 * [go-multierror](https://github.com/hashicorp/go-multierror) available under [license](https://github.com/hashicorp/go-multierror/blob/master/LICENSE) 
 * [html2text](https://github.com/jaytaylor/html2text) available under [license](https://github.com/jaytaylor/html2text/blob/master/LICENSE) 
+* [go-locale](https://github.com/jeandeaual/go-locale) available under [license](https://github.com/jeandeaual/go-locale/blob/master/LICENSE) 
 * [go-keychain](https://github.com/keybase/go-keychain) available under [license](https://github.com/keybase/go-keychain/blob/master/LICENSE) 
 * [dns](https://github.com/miekg/dns) available under [license](https://github.com/miekg/dns/blob/master/LICENSE) 
+* [memory](https://github.com/pbnjay/memory) available under [license](https://github.com/pbnjay/memory/blob/master/LICENSE) 
 * [errors](https://github.com/pkg/errors) available under [license](https://github.com/pkg/errors/blob/master/LICENSE) 
 * [profile](https://github.com/pkg/profile) available under [license](https://github.com/pkg/profile/blob/master/LICENSE) 
 * [logrus](https://github.com/sirupsen/logrus) available under [license](https://github.com/sirupsen/logrus/blob/master/LICENSE) 
 * [testify](https://github.com/stretchr/testify) available under [license](https://github.com/stretchr/testify/blob/master/LICENSE) 
 * [cli](https://github.com/urfave/cli/v2) available under [license](https://github.com/urfave/cli/v2/blob/master/LICENSE) 
 * [msgpack](https://github.com/vmihailenco/msgpack/v5) available under [license](https://github.com/vmihailenco/msgpack/v5/blob/master/LICENSE) 
-* [goleak](https://go.uber.org/goleak)
+* [goleak](https://go.uber.org/goleak) available under [license](https://pkg.go.dev/go.uber.org/goleak?tab=licenses) 
 * [exp](https://golang.org/x/exp) available under [license](https://cs.opensource.google/go/x/exp/+/master:LICENSE) 
 * [net](https://golang.org/x/net) available under [license](https://cs.opensource.google/go/x/net/+/master:LICENSE) 
+* [oauth2](https://golang.org/x/oauth2) available under [license](https://cs.opensource.google/go/x/oauth2/+/master:LICENSE) 
 * [sys](https://golang.org/x/sys) available under [license](https://cs.opensource.google/go/x/sys/+/master:LICENSE) 
 * [text](https://golang.org/x/text) available under [license](https://cs.opensource.google/go/x/text/+/master:LICENSE) 
+* [api](https://google.golang.org/api) available under [license](https://pkg.go.dev/google.golang.org/api?tab=licenses) 
 * [grpc](https://google.golang.org/grpc) available under [license](https://github.com/grpc/grpc-go/blob/master/LICENSE) 
 * [protobuf](https://google.golang.org/protobuf) available under [license](https://github.com/protocolbuffers/protobuf/blob/main/LICENSE) 
 * [plist](https://howett.net/plist) available under [license](https://github.com/DHowett/go-plist/blob/main/LICENSE) 
-* [atlas](https://ariga.io/atlas)
-* [ent](https://entgo.io/ent)
+* [compute](https://cloud.google.com/go/compute) available under [license](https://pkg.go.dev/cloud.google.com/go/compute?tab=licenses) 
+* [metadata](https://cloud.google.com/go/compute/metadata) available under [license](https://pkg.go.dev/cloud.google.com/go/compute/metadata?tab=licenses) 
 * [bcrypt](https://github.com/ProtonMail/bcrypt) available under [license](https://github.com/ProtonMail/bcrypt/blob/master/LICENSE) 
 * [go-crypto](https://github.com/ProtonMail/go-crypto) available under [license](https://github.com/ProtonMail/go-crypto/blob/master/LICENSE) 
 * [go-mime](https://github.com/ProtonMail/go-mime) available under [license](https://github.com/ProtonMail/go-mime/blob/master/LICENSE) 
 * [go-srp](https://github.com/ProtonMail/go-srp) available under [license](https://github.com/ProtonMail/go-srp/blob/master/LICENSE) 
 * [readline](https://github.com/abiosoft/readline) available under [license](https://github.com/abiosoft/readline/blob/master/LICENSE) 
-* [levenshtein](https://github.com/agext/levenshtein) available under [license](https://github.com/agext/levenshtein/blob/master/LICENSE) 
 * [cascadia](https://github.com/andybalholm/cascadia) available under [license](https://github.com/andybalholm/cascadia/blob/master/LICENSE) 
-* [antlr](https://github.com/antlr/antlr4/runtime/Go/antlr) available under [license](https://github.com/antlr/antlr4/runtime/Go/antlr/blob/master/LICENSE) 
-* [go-textseg](https://github.com/apparentlymart/go-textseg/v13) available under [license](https://github.com/apparentlymart/go-textseg/v13/blob/master/LICENSE) 
+* [sonic](https://github.com/bytedance/sonic) available under [license](https://github.com/bytedance/sonic/blob/master/LICENSE) 
+* [base64x](https://github.com/chenzhuoyu/base64x) available under [license](https://github.com/chenzhuoyu/base64x/blob/master/LICENSE) 
 * [test](https://github.com/chzyer/test) available under [license](https://github.com/chzyer/test/blob/master/LICENSE) 
 * [circl](https://github.com/cloudflare/circl) available under [license](https://github.com/cloudflare/circl/blob/master/LICENSE) 
 * [go-md2man](https://github.com/cpuguy83/go-md2man/v2) available under [license](https://github.com/cpuguy83/go-md2man/v2/blob/master/LICENSE) 
@@ -87,51 +89,60 @@ Proton Mail Bridge includes the following 3rd party software:
 * [go-spew](https://github.com/davecgh/go-spew) available under [license](https://github.com/davecgh/go-spew/blob/master/LICENSE) 
 * [go-windows](https://github.com/elastic/go-windows) available under [license](https://github.com/elastic/go-windows/blob/master/LICENSE) 
 * [go-textwrapper](https://github.com/emersion/go-textwrapper) available under [license](https://github.com/emersion/go-textwrapper/blob/master/LICENSE) 
-* [go-vcard](https://github.com/emersion/go-vcard) available under [license](https://github.com/emersion/go-vcard/blob/master/LICENSE) 
+* [fgprof](https://github.com/felixge/fgprof) available under [license](https://github.com/felixge/fgprof/blob/master/LICENSE) 
 * [go-shlex](https://github.com/flynn-archive/go-shlex) available under [license](https://github.com/flynn-archive/go-shlex/blob/master/LICENSE) 
+* [mimetype](https://github.com/gabriel-vasile/mimetype) available under [license](https://github.com/gabriel-vasile/mimetype/blob/master/LICENSE) 
 * [sse](https://github.com/gin-contrib/sse) available under [license](https://github.com/gin-contrib/sse/blob/master/LICENSE) 
 * [gin](https://github.com/gin-gonic/gin) available under [license](https://github.com/gin-gonic/gin/blob/master/LICENSE) 
-* [inflect](https://github.com/go-openapi/inflect) available under [license](https://github.com/go-openapi/inflect/blob/master/LICENSE) 
 * [locales](https://github.com/go-playground/locales) available under [license](https://github.com/go-playground/locales/blob/master/LICENSE) 
 * [universal-translator](https://github.com/go-playground/universal-translator) available under [license](https://github.com/go-playground/universal-translator/blob/master/LICENSE) 
 * [validator](https://github.com/go-playground/validator/v10) available under [license](https://github.com/go-playground/validator/v10/blob/master/LICENSE) 
+* [go-json](https://github.com/goccy/go-json) available under [license](https://github.com/goccy/go-json/blob/master/LICENSE) 
 * [uuid](https://github.com/gofrs/uuid) available under [license](https://github.com/gofrs/uuid/blob/master/LICENSE) 
+* [groupcache](https://github.com/golang/groupcache) available under [license](https://github.com/golang/groupcache/blob/master/LICENSE) 
 * [protobuf](https://github.com/golang/protobuf) available under [license](https://github.com/golang/protobuf/blob/master/LICENSE) 
+* [pprof](https://github.com/google/pprof) available under [license](https://github.com/google/pprof/blob/master/LICENSE) 
+* [enterprise-certificate-proxy](https://github.com/googleapis/enterprise-certificate-proxy) available under [license](https://github.com/googleapis/enterprise-certificate-proxy/blob/master/LICENSE) 
+* [gax-go](https://github.com/googleapis/gax-go/v2) available under [license](https://github.com/googleapis/gax-go/v2/blob/master/LICENSE) 
 * [errwrap](https://github.com/hashicorp/errwrap) available under [license](https://github.com/hashicorp/errwrap/blob/master/LICENSE) 
 * [go-immutable-radix](https://github.com/hashicorp/go-immutable-radix) available under [license](https://github.com/hashicorp/go-immutable-radix/blob/master/LICENSE) 
 * [go-memdb](https://github.com/hashicorp/go-memdb) available under [license](https://github.com/hashicorp/go-memdb/blob/master/LICENSE) 
 * [golang-lru](https://github.com/hashicorp/golang-lru) available under [license](https://github.com/hashicorp/golang-lru/blob/master/LICENSE) 
-* [hcl](https://github.com/hashicorp/hcl/v2) available under [license](https://github.com/hashicorp/hcl/v2/blob/master/LICENSE) 
 * [multierror](https://github.com/joeshaw/multierror) available under [license](https://github.com/joeshaw/multierror/blob/master/LICENSE) 
 * [go](https://github.com/json-iterator/go) available under [license](https://github.com/json-iterator/go/blob/master/LICENSE) 
+* [cpuid](https://github.com/klauspost/cpuid/v2) available under [license](https://github.com/klauspost/cpuid/v2/blob/master/LICENSE) 
 * [go-urn](https://github.com/leodido/go-urn) available under [license](https://github.com/leodido/go-urn/blob/master/LICENSE) 
 * [go-colorable](https://github.com/mattn/go-colorable) available under [license](https://github.com/mattn/go-colorable/blob/master/LICENSE) 
 * [go-isatty](https://github.com/mattn/go-isatty) available under [license](https://github.com/mattn/go-isatty/blob/master/LICENSE) 
 * [go-runewidth](https://github.com/mattn/go-runewidth) available under [license](https://github.com/mattn/go-runewidth/blob/master/LICENSE) 
 * [go-sqlite3](https://github.com/mattn/go-sqlite3) available under [license](https://github.com/mattn/go-sqlite3/blob/master/LICENSE) 
-* [go-wordwrap](https://github.com/mitchellh/go-wordwrap) available under [license](https://github.com/mitchellh/go-wordwrap/blob/master/LICENSE) 
 * [concurrent](https://github.com/modern-go/concurrent) available under [license](https://github.com/modern-go/concurrent/blob/master/LICENSE) 
 * [reflect2](https://github.com/modern-go/reflect2) available under [license](https://github.com/modern-go/reflect2/blob/master/LICENSE) 
 * [tablewriter](https://github.com/olekukonko/tablewriter) available under [license](https://github.com/olekukonko/tablewriter/blob/master/LICENSE) 
 * [go-toml](https://github.com/pelletier/go-toml/v2) available under [license](https://github.com/pelletier/go-toml/v2/blob/master/LICENSE) 
+* [lz4](https://github.com/pierrec/lz4/v4) available under [license](https://github.com/pierrec/lz4/v4/blob/master/LICENSE) 
 * [go-difflib](https://github.com/pmezard/go-difflib) available under [license](https://github.com/pmezard/go-difflib/blob/master/LICENSE) 
 * [procfs](https://github.com/prometheus/procfs) available under [license](https://github.com/prometheus/procfs/blob/master/LICENSE) 
 * [uniseg](https://github.com/rivo/uniseg) available under [license](https://github.com/rivo/uniseg/blob/master/LICENSE) 
 * [blackfriday](https://github.com/russross/blackfriday/v2) available under [license](https://github.com/russross/blackfriday/v2/blob/master/LICENSE) 
 * [pflag](https://github.com/spf13/pflag) available under [license](https://github.com/spf13/pflag/blob/master/LICENSE) 
 * [bom](https://github.com/ssor/bom) available under [license](https://github.com/ssor/bom/blob/master/LICENSE) 
+* [golang-asm](https://github.com/twitchyliquid64/golang-asm) available under [license](https://github.com/twitchyliquid64/golang-asm/blob/master/LICENSE) 
 * [codec](https://github.com/ugorji/go/codec) available under [license](https://github.com/ugorji/go/codec/blob/master/LICENSE) 
 * [tagparser](https://github.com/vmihailenco/tagparser/v2) available under [license](https://github.com/vmihailenco/tagparser/v2/blob/master/LICENSE) 
 * [smetrics](https://github.com/xrash/smetrics) available under [license](https://github.com/xrash/smetrics/blob/master/LICENSE) 
-* [go-cty](https://github.com/zclconf/go-cty) available under [license](https://github.com/zclconf/go-cty/blob/master/LICENSE) 
+* [go-ordered-json](https://gitlab.com/c0b/go-ordered-json) available under [license](https://gitlab.com/c0b/go-ordered-json/blob/master/LICENSE) 
+* [go.opencensus.io](https://pkg.go.dev/go.opencensus.io?tab=licenses) available under [license](https://pkg.go.dev/go.opencensus.io?tab=licenses) 
+* [arch](https://golang.org/x/arch) available under [license](https://cs.opensource.google/go/x/arch/+/master:LICENSE) 
 * [crypto](https://golang.org/x/crypto) available under [license](https://cs.opensource.google/go/x/crypto/+/master:LICENSE) 
 * [mod](https://golang.org/x/mod) available under [license](https://cs.opensource.google/go/x/mod/+/master:LICENSE) 
 * [sync](https://golang.org/x/sync) available under [license](https://cs.opensource.google/go/x/sync/+/master:LICENSE) 
 * [tools](https://golang.org/x/tools) available under [license](https://cs.opensource.google/go/x/tools/+/master:LICENSE) 
-* [genproto](https://google.golang.org/genproto)
-gopkg.in/yaml.v2
-gopkg.in/yaml.v3
-* [docker-credential-helpers](https://github.com/ProtonMail/docker-credential-helpers) available under [license](https://github.com/ProtonMail/docker-credential-helpers/blob/master/LICENSE) 
+* [appengine](https://google.golang.org/appengine) available under [license](https://pkg.go.dev/google.golang.org/appengine?tab=licenses) 
+* [genproto](https://google.golang.org/genproto) available under [license](https://pkg.go.dev/google.golang.org/genproto?tab=licenses) 
+* [yaml](https://gopkg.in/yaml.v3) available under [license](https://github.com/go-yaml/yaml/blob/v3.0.1/LICENSE)  available under [license](https://github.com/go-yaml/yaml/blob/v3.0.1/LICENSE) 
 * [go-message](https://github.com/ProtonMail/go-message) available under [license](https://github.com/ProtonMail/go-message/blob/master/LICENSE) 
+* [go-smtp](https://github.com/ProtonMail/go-smtp) available under [license](https://github.com/ProtonMail/go-smtp/blob/master/LICENSE) 
+* [resty](https://github.com/LBeernaertProton/resty/v2) available under [license](https://github.com/LBeernaertProton/resty/v2/blob/master/LICENSE) 
 * [go-keychain](https://github.com/cuthix/go-keychain) available under [license](https://github.com/cuthix/go-keychain/blob/master/LICENSE) 
 <!-- END AUTOGEN -->

Makefile

@@ -1,17 +1,18 @@
 export GO111MODULE=on
+export CGO_ENABLED=1
 
 # By default, the target OS is the same as the host OS,
 # but this can be overridden by setting TARGET_OS to "windows"/"darwin"/"linux".
 GOOS:=$(shell go env GOOS)
 TARGET_CMD?=Desktop-Bridge
 TARGET_OS?=${GOOS}
-ROOT_DIR:=$(shell dirname $(realpath $(firstword $(MAKEFILE_LIST))))
+ROOT_DIR:=$(realpath .)
 
 ## Build
 .PHONY: build build-gui build-nogui build-launcher versioner hasher
 
 # Keep version hardcoded so app build works also without Git repository.
-BRIDGE_APP_VERSION?=3.0.15+git
+BRIDGE_APP_VERSION?=3.18.0+git
 APP_VERSION:=${BRIDGE_APP_VERSION}
 APP_FULL_NAME:=Proton Mail Bridge
 APP_VENDOR:=Proton AG
@@ -19,20 +20,26 @@ SRC_ICO:=bridge.ico
 SRC_ICNS:=Bridge.icns
 SRC_SVG:=bridge.svg
 EXE_NAME:=proton-bridge
-REVISION:=$(shell git rev-parse --short=10 HEAD)
+REVISION:=$(shell "${ROOT_DIR}/utils/get_revision.sh" rev)
+TAG:=$(shell "${ROOT_DIR}/utils/get_revision.sh" tag)
 BUILD_TIME:=$(shell date +%FT%T%z)
 MACOS_MIN_VERSION_ARM64=11.0
 MACOS_MIN_VERSION_AMD64=10.15
+BUILD_ENV?=dev
 
 BUILD_FLAGS:=-tags='${BUILD_TAGS}'
 BUILD_FLAGS_LAUNCHER:=${BUILD_FLAGS}
-BUILD_FLAGS_GUI:=-tags='${BUILD_TAGS} build_qt'
-GO_LDFLAGS:=$(addprefix -X github.com/ProtonMail/proton-bridge/v3/internal/constants., Version=${APP_VERSION} Revision=${REVISION} BuildTime=${BUILD_TIME})
+GO_LDFLAGS:=$(addprefix -X github.com/ProtonMail/proton-bridge/v3/internal/constants., Version=${APP_VERSION} Revision=${REVISION} Tag=${TAG} BuildTime=${BUILD_TIME})
 GO_LDFLAGS+=-X "github.com/ProtonMail/proton-bridge/v3/internal/constants.FullAppName=${APP_FULL_NAME}"
 
-ifneq "${BUILD_LDFLAGS}" ""
-	GO_LDFLAGS+=${BUILD_LDFLAGS}
+ifneq "${DSN_SENTRY}" ""
+	GO_LDFLAGS+=-X github.com/ProtonMail/proton-bridge/v3/internal/constants.DSNSentry=${DSN_SENTRY}
 endif
+
+ifneq "${BUILD_ENV}" ""
+	GO_LDFLAGS+=-X github.com/ProtonMail/proton-bridge/v3/internal/constants.BuildEnv=${BUILD_ENV}
+endif
+
 GO_LDFLAGS_LAUNCHER:=${GO_LDFLAGS}
 ifeq "${TARGET_OS}" "windows"
 	#GO_LDFLAGS+=-H=windowsgui # Disabled so we can inspect trace logs from the bridge for debugging.
@@ -40,7 +47,6 @@ ifeq "${TARGET_OS}" "windows"
 endif
 
 BUILD_FLAGS+=-ldflags '${GO_LDFLAGS}'
-BUILD_FLAGS_GUI+=-ldflags "${GO_LDFLAGS}"
 BUILD_FLAGS_LAUNCHER+=-ldflags '${GO_LDFLAGS_LAUNCHER}'
 DEPLOY_DIR:=cmd/${TARGET_CMD}/deploy
 DIRNAME:=$(shell basename ${CURDIR})
@@ -96,9 +102,9 @@ endif
 
 ifeq "${GOOS}" "windows"
 	go-build-finalize= \
-		powershell Copy-Item ${ROOT_DIR}/${RESOURCE_FILE} ${4}  && \
-		$(call go-build,$(1),$(2),$(3)) && \
-		powershell Remove-Item ${4} -Force
+		$(if $(4),cp "${ROOT_DIR}/${RESOURCE_FILE}" ${4}  &&,) \
+		$(call go-build,$(1),$(2),$(3)) \
+		$(if $(4), && rm -f ${4},)
 endif
 
 ${EXE_NAME}: gofiles  ${RESOURCE_FILE}
@@ -112,7 +118,10 @@ versioner:
 	go build ${BUILD_FLAGS} -o versioner utils/versioner/main.go
 
 vault-editor:
-	go build -tags debug -o vault-editor utils/vault-editor/main.go
+	$(call go-build-finalize,-tags=debug,"vault-editor","./utils/vault-editor/main.go")
+
+bridge-rollout:
+	$(call go-build-finalize,, "bridge-rollout","./utils/bridge-rollout/bridge-rollout.go")
 
 hasher:
 	go build -o hasher utils/hasher/main.go
@@ -154,9 +163,12 @@ ${EXE_TARGET}: check-build-essentials ${EXE_NAME}
 		BRIDGE_VENDOR="${APP_VENDOR}" \
 		BRIDGE_APP_VERSION=${APP_VERSION} \
 		BRIDGE_REVISION=${REVISION} \
+		BRIDGE_TAG=${TAG} \
+		BRIDGE_DSN_SENTRY=${DSN_SENTRY} \
  		BRIDGE_BUILD_TIME=${BUILD_TIME} \
 		BRIDGE_GUI_BUILD_CONFIG=Release \
-		BRIDGE_INSTALL_PATH=${ROOT_DIR}/${DEPLOY_DIR}/${GOOS} \
+		BRIDGE_BUILD_ENV=${BUILD_ENV} \
+		BRIDGE_INSTALL_PATH="${ROOT_DIR}/${DEPLOY_DIR}/${GOOS}" \
 		./build.sh install
 	mv "${ROOT_DIR}/${BRIDGE_EXE}" "$(ROOT_DIR)/${EXE_TARGET}"
 
@@ -177,7 +189,7 @@ ${RESOURCE_FILE}: ./dist/info.rc ./dist/${SRC_ICO} .FORCE
 
 ## Dev dependencies
 .PHONY: install-devel-tools install-linter install-go-mod-outdated install-git-hooks
-LINTVER:="v1.50.0"
+LINTVER:="v1.61.0"
 LINTSRC:="https://raw.githubusercontent.com/golangci/golangci-lint/master/install.sh"
 
 install-dev-dependencies: install-devel-tools install-linter install-go-mod-outdated
@@ -221,14 +233,28 @@ add-license:
 change-copyright-year:
 	./utils/missing_license.sh change-year
 
+GOCOVERAGE=-covermode=count -coverpkg=github.com/ProtonMail/proton-bridge/v3/internal/...,github.com/ProtonMail/proton-bridge/v3/pkg/...,
+GOCOVERDIR=-args -test.gocoverdir=$$PWD/coverage
+
 test: gofiles
-	go test -v -timeout=5m -p=1 -count=1 -coverprofile=/tmp/coverage.out -run=${TESTRUN} ./internal/... ./pkg/...
+	mkdir -p coverage/unit-${GOOS}
+	go test \
+		-v -timeout=20m -p=1 -count=1 \
+		${GOCOVERAGE} \
+		-run=${TESTRUN} ./internal/... ./pkg/... \
+		${GOCOVERDIR}/unit-${GOOS}
 
 test-race: gofiles
-	go test -v -timeout=30m -p=1 -count=1 -race -failfast -run=${TESTRUN} ./internal/... ./pkg/...
+	go test -v -timeout=40m -p=1 -count=1 -race -failfast -run=${TESTRUN} ./internal/... ./pkg/...
 
 test-integration: gofiles
-	go test -v -timeout=10m -p=1 -count=1 github.com/ProtonMail/proton-bridge/v3/tests
+	mkdir -p coverage/integration
+	go test \
+		-v -timeout=60m -p=1 -count=1 -tags=test_integration \
+		${GOCOVERAGE} \
+		github.com/ProtonMail/proton-bridge/v3/tests \
+		${GOCOVERDIR}/integration
+
 
 test-integration-debug: gofiles
 	dlv test github.com/ProtonMail/proton-bridge/v3/tests -- -test.v -test.timeout=10m -test.parallel=1 -test.count=1
@@ -236,6 +262,23 @@ test-integration-debug: gofiles
 test-integration-race: gofiles
 	go test -v -timeout=60m -p=1 -count=1 -race -failfast github.com/ProtonMail/proton-bridge/v3/tests
 
+test-integration-nightly: gofiles
+	mkdir -p coverage/integration
+	gotestsum \
+		--junitfile tests/result/feature-tests.xml -- \
+		-v -timeout=90m -p=1 -count=1 -tags=test_integration \
+		${GOCOVERAGE} \
+		github.com/ProtonMail/proton-bridge/v3/tests \
+		${GOCOVERDIR}/integration \
+		nightly
+
+fuzz: gofiles
+	go test -fuzz=FuzzUnmarshal 	 -parallel=4 -fuzztime=60s $(PWD)/internal/legacy/credentials
+	go test -fuzz=FuzzNewParser 	 -parallel=4 -fuzztime=60s $(PWD)/pkg/message/parser
+	go test -fuzz=FuzzReadHeaderBody -parallel=4 -fuzztime=60s $(PWD)/pkg/message
+	go test -fuzz=FuzzDecodeHeader 	 -parallel=4 -fuzztime=60s $(PWD)/pkg/mime
+	go test -fuzz=FuzzDecodeCharset  -parallel=4 -fuzztime=60s $(PWD)/pkg/mime
+
 bench:
 	go test -run '^$$' -bench=. -memprofile bench_mem.pprof -cpuprofile bench_cpu.pprof ./internal/store
 	go tool pprof -png -output bench_mem.png bench_mem.pprof
@@ -247,11 +290,28 @@ coverage: test
 mocks:
 	mockgen --package mocks github.com/ProtonMail/proton-bridge/v3/internal/bridge TLSReporter,ProxyController,Autostarter > tmp
 	mv tmp internal/bridge/mocks/mocks.go
-	mockgen --package mocks github.com/ProtonMail/proton-bridge/v3/internal/async PanicHandler > internal/bridge/mocks/async_mocks.go
+	mockgen --package mocks github.com/ProtonMail/gluon/async PanicHandler > internal/bridge/mocks/async_mocks.go
 	mockgen --package mocks github.com/ProtonMail/gluon/reporter Reporter > internal/bridge/mocks/gluon_mocks.go
 	mockgen --package mocks github.com/ProtonMail/proton-bridge/v3/internal/updater Downloader,Installer > internal/updater/mocks/mocks.go
+	mockgen --package mocks github.com/ProtonMail/proton-bridge/v3/internal/telemetry HeartbeatManager > internal/telemetry/mocks/mocks.go
+	cp internal/telemetry/mocks/mocks.go internal/bridge/mocks/telemetry_mocks.go
+	mockgen --package mocks github.com/ProtonMail/proton-bridge/v3/internal/services/userevents \
+EventSource,EventIDStore  > internal/services/userevents/mocks/mocks.go
+	mockgen --package userevents github.com/ProtonMail/proton-bridge/v3/internal/services/userevents \
+EventSubscriber,MessageEventHandler,LabelEventHandler,AddressEventHandler,RefreshEventHandler,UserEventHandler,UserUsedSpaceEventHandler > tmp
+	mv tmp internal/services/userevents/mocks_test.go
+	mockgen --package mocks github.com/ProtonMail/proton-bridge/v3/internal/events EventPublisher \
+> internal/events/mocks/mocks.go
+	mockgen --package mocks github.com/ProtonMail/proton-bridge/v3/internal/services/useridentity IdentityProvider,Telemetry \
+> internal/services/useridentity/mocks/mocks.go
+	mockgen --self_package "github.com/ProtonMail/proton-bridge/v3/internal/services/syncservice" -package syncservice github.com/ProtonMail/proton-bridge/v3/internal/services/syncservice \
+ApplyStageInput,BuildStageInput,BuildStageOutput,DownloadStageInput,DownloadStageOutput,MetadataStageInput,MetadataStageOutput,\
+StateProvider,Regulator,UpdateApplier,MessageBuilder,APIClient,Reporter,DownloadRateModifier \
+> tmp
+	mv tmp internal/services/syncservice/mocks_test.go
+	mockgen --package mocks github.com/ProtonMail/gluon/connector IMAPStateWrite > internal/services/imapservice/mocks/mocks.go
 
-lint: gofiles lint-golang lint-license lint-dependencies lint-changelog
+lint: gofiles lint-golang lint-license lint-dependencies lint-changelog lint-bug-report
 
 lint-license:
 	./utils/missing_license.sh check
@@ -267,12 +327,11 @@ lint-golang:
 	$(info linting with GOMAXPROCS=${GOMAXPROCS})
 	golangci-lint run ./...
 
-gobinsec: gobinsec-cache.yml build
-	gobinsec -wait -cache -config utils/gobinsec_conf.yml ${EXE_TARGET} ${DEPLOY_DIR}/${TARGET_OS}/${LAUNCHER_EXE}
+lint-bug-report:
+	python3 utils/validate_bug_report_file.py --file "internal/frontend/bridge-gui/bridge-gui/qml/Resources/bug_report_flow.json"
 
-gobinsec-cache.yml:
-	./utils/gobinsec_update.sh
-	cp ./utils/gobinsec_update/gobinsec-cache-valid.yml ./gobinsec-cache.yml
+lint-bug-report-preview:
+	python3 utils/validate_bug_report_file.py --file "internal/frontend/bridge-gui/bridge-gui/qml/Resources/bug_report_flow.json" --preview
 
 updates: install-go-mod-outdated
 	# Uncomment the "-ci" to fail the job if something can be updated.
@@ -319,7 +378,11 @@ run-nogui: build-nogui clean-vendor gofiles
 	PROTONMAIL_ENV=dev ./${LAUNCHER_EXE} ${RUN_FLAGS} -c
 
 run-debug:
-	dlv debug ./cmd/Desktop-Bridge/main.go -- -l=debug
+	dlv debug \
+		--build-flags "-ldflags '-X github.com/ProtonMail/proton-bridge/v3/internal/constants.Version=3.1.0+git'" \
+		./cmd/Desktop-Bridge/main.go \
+		-- \
+		-n -l=trace
 
 ifeq "${TARGET_OS}" "windows"
 	EXE_SUFFIX=.exe
@@ -340,7 +403,7 @@ clean-vendor:
 
 clean-gui:
 	cd internal/frontend/bridge-gui/ && \
-		rm -f Version.h && \
+		rm -f BuildConfig.h && \
 		rm -rf cmake-build-*/
 
 clean-vcpkg:
@@ -363,6 +426,6 @@ clean: clean-vendor clean-gui clean-vcpkg
 .PHONY: generate
 generate:
 	go generate ./...
-	$(MAKE) add-license
+	$(MAKE) build
 
 .FORCE:

README.md

@@ -1,7 +1,7 @@
-# Proton Mail Bridge and Import Export app
-Copyright (c) 2022 Proton AG
+# Proton Mail Bridge
+Copyright (c) 2025 Proton AG
 
-This repository holds the Proton Mail Bridge and the Proton Mail Import-Export applications.
+This repository holds the Proton Mail Bridge application.
 For a detailed build information see [BUILDS](./BUILDS.md).
 The license can be found in [LICENSE](./LICENSE) file, for more licensing information see [COPYING_NOTES](./COPYING_NOTES.md).
 For contribution policy see [CONTRIBUTING](./CONTRIBUTING.md).
@@ -13,7 +13,7 @@ Proton Mail Bridge for e-mail clients.
 When launched, Bridge will initialize local IMAP/SMTP servers and render 
 its GUI.
 
-To configure an e-mail client, firstly log in using your Proton Mail credentials. 
+To configure an e-mail client, first log in using your Proton Mail credentials. 
 Open your e-mail client and add a new account using the settings which are 
 located in the Bridge GUI. The client will only be able to sync with 
 your Proton Mail account when the Bridge is running, thus the option 
@@ -24,10 +24,10 @@ background.
 
 More details [on the public website](https://proton.me/mail/bridge).
 
-## Launchers
-Launchers are binaries used to run the Proton Mail Bridge or Import-Export apps.
+## Launcher
+The launcher is a binary used to run the Proton Mail Bridge.
 
-Official distributions of the Proton Mail Bridge and Import-Export apps contain
+The Official distribution of the Proton Mail Bridge application contains
 both a launcher and the app itself. The launcher is installed in a protected
 area of the system (i.e. an area accessible only with admin privileges) and is
 used to run the app. The launcher ensures that nobody tampered with the app's
@@ -37,7 +37,7 @@ feature enables the app to securely update itself automatically without asking
 the user for a password.
 
 ## Keychain
-You need to have a keychain in order to run the Proton Mail Bridge. On Mac or
+You need to have a keychain in order to run Proton Mail Bridge. On Mac or
 Windows, Bridge uses native credential managers. On Linux, use `secret-service` freedesktop.org API
 (e.g. [Gnome keyring](https://wiki.gnome.org/Projects/GnomeKeyring/))
 or
@@ -48,9 +48,6 @@ major problems.
 
 ## Environment Variables
 
-### Bridge application
-- `BRIDGESTRICTMODE`: tells bridge to turn on `bbolt`'s "strict mode" which checks the database after every `Commit`. Set to `1` to enable.
-
 ### Dev build or run
 - `APP_VERSION`: set the bridge app version used during testing or building
 - `PROTONMAIL_ENV`: when set to `dev` it is not using Sentry to report crashes
@@ -78,17 +75,18 @@ There are now three types of system folders which Bridge recognises:
 ## Files
 
 |                        | Base Dir | Path                       |
-|-----------------------|----------|----------------------------|
+|------------------------|----------|----------------------------|
 | bridge lock file       | cache    | bridge.lock                |
 | bridge-gui lock file   | cache    | bridge-gui.lock            |
 | vault                  | config   | vault.enc                  |
 | gRPC server json       | config   | grpcServerConfig.json      |
 | gRPC client json       | config   | grpcClientConfig_<id>.json |
+| gRPC Focus server json | config   | grpcFocusServerConfig.json |
 | Logs                   | data     | logs                       |
 | gluon DB               | data     | gluon/backend/db           |
-| gluon messages        | sata     | gluon/backend/store        |
+| gluon messages         | data     | gluon/backend/store        |
 | Update files           | data     | updates                    |
 | sentry cache           | data     | sentry_cache               |
-| Mac/Linux File Socket | temp     | bridge_{RANDOM_UUID}.sock  |
+| Mac/Linux File Socket  | temp     | bridge{4_DIGITS}           |
 
 

ci/build.yml

@@ -0,0 +1,72 @@
+---
+
+.script-build:
+  stage: build
+  needs: ["lint"]
+  extends:
+    - .rules-branch-and-MR-manual
+  script:
+    - which go && go version
+    - which gcc && gcc --version
+    - which qmake && qmake --version
+    - git rev-parse --short=10 HEAD
+    - make build
+    - git diff && git diff-index --quiet HEAD
+    - make vault-editor
+    - make bridge-rollout
+  artifacts:
+    expire_in: 1 day
+    when: always
+    name: "$CI_JOB_NAME-$CI_COMMIT_SHORT_SHA"
+    paths:
+      - bridge_*.tgz
+      - vault-editor
+      - bridge-rollout
+build-linux:
+  extends:
+    - .script-build
+    - .env-linux-build
+
+build-linux-qa:
+  extends:
+    - build-linux
+    - .rules-branch-manual-MR-and-devel-always
+  variables:
+    BUILD_TAGS: "build_qa"
+
+build-darwin:
+  extends:
+    - .script-build
+    - .env-darwin
+
+build-darwin-qa:
+  extends:
+    - build-darwin
+  variables:
+    BUILD_TAGS: "build_qa"
+
+build-windows:
+  extends:
+    - .script-build
+    - .env-windows
+
+build-windows-qa:
+  extends:
+    - build-windows
+  variables:
+    BUILD_TAGS: "build_qa"
+
+trigger-qa-installer:
+  stage: build
+  needs: ["lint"]
+  extends:
+    - .rules-br-tag-always-branch-and-MR-manual
+  variables:
+    APP: bridge
+    WORKFLOW: build-all
+    SRC_TAG: $CI_COMMIT_BRANCH
+    TAG: $CI_COMMIT_TAG
+    SRC_HASH: $CI_COMMIT_SHA
+  trigger:
+    project: "jcuth/bridge-release"
+    branch: master

ci/env.yml

@@ -0,0 +1,59 @@
+
+---
+
+.env-windows:
+  extends:
+    - .image-windows-virt-build
+  before_script:
+    - !reference [.before-script-windows-virt-build, before_script]
+    - !reference [.before-script-git-config, before_script]
+    - mkdir -p .cache/bin
+    - export PATH=$(pwd)/.cache/bin:$PATH
+    - export GOPATH="$CI_PROJECT_DIR/.cache"
+  variables:
+    GOARCH: amd64
+    BRIDGE_SYNC_FORCE_MINIMUM_SPEC: 1
+    VCPKG_DEFAULT_BINARY_CACHE: ${CI_PROJECT_DIR}/.cache
+  cache:
+    key: windows-vcpkg-go-0
+    paths:
+      - .cache
+    when: 'always'
+
+.env-darwin:
+  extends:
+    - .image-darwin-build
+  before_script:
+    - !reference [.before-script-darwin-tart-build, before_script]
+    - !reference [.before-script-git-config, before_script]
+    - mkdir -p .cache/bin
+    - export PATH=$(pwd)/.cache/bin:$PATH
+    - export GOPATH="$CI_PROJECT_DIR/.cache"
+  variables:
+    BRIDGE_SYNC_FORCE_MINIMUM_SPEC: 1
+    VCPKG_DEFAULT_BINARY_CACHE: ${CI_PROJECT_DIR}/.cache
+  cache:
+    key: darwin-go-and-vcpkg
+    paths:
+      - .cache
+    when: 'always'
+
+.env-linux-build:
+  extends:
+    - .image-linux-build
+  variables:
+    VCPKG_DEFAULT_BINARY_CACHE: ${CI_PROJECT_DIR}/.cache
+  cache:
+    key: linux-vcpkg
+    paths:
+      - .cache
+    when: 'always'
+  before_script:
+    - export BRIDGE_SYNC_FORCE_MINIMUM_SPEC=1
+    - !reference [.before-script-git-config, before_script]
+    - mkdir -p .cache/bin
+    - export PATH=$(pwd)/.cache/bin:$PATH
+    - export GOPATH="$CI_PROJECT_DIR/.cache"
+  tags:
+    - shared-large
+

ci/report.yml

@@ -0,0 +1,25 @@
+
+---
+
+include:
+  - project: 'tpe/testmo-reporter'
+    ref: master
+    file: '/scenarios/testmo-script.yml'
+
+testmo-upload:
+    stage: report
+    extends:
+      - .testmo-upload
+      - .rules-branch-manual-scheduled-and-test-branch-always
+    needs:
+      - test-integration-nightly
+    before_script: []
+    variables:
+      TESTMO_TOKEN: "$TESTMO_TOKEN"
+      TESTMO_URL: "https://proton.testmo.net"
+      PROJECT_ID: "9"
+      NAME: "Nightly integration tests"
+      MILESTONE: "Nightly integration tests"
+      SOURCE: "test-integration-nightly"
+      TAGS: "$CI_COMMIT_REF_SLUG"
+      RESULT_FOLDER: "tests/result/*.xml"

ci/rules.yml

@@ -0,0 +1,58 @@
+
+---
+
+.rules-branch-and-MR-manual:
+  rules:
+    - if: $CI_COMMIT_BRANCH ||  $CI_PIPELINE_SOURCE == "merge_request_event"
+      when: manual
+      allow_failure: true
+    - when: never
+
+.rules-branch-manual-MR-and-devel-always:
+  rules:
+    - if: $CI_COMMIT_BRANCH == "devel" || $CI_PIPELINE_SOURCE == "merge_request_event"
+      when: always
+      allow_failure: false
+    - if: $CI_COMMIT_BRANCH
+      when: manual
+      allow_failure: true
+    - when: never
+
+.rules-branch-manual-br-tag-and-MR-and-devel-always:
+  rules:
+    - if: $CI_COMMIT_BRANCH == "devel" || $CI_PIPELINE_SOURCE == "merge_request_event"
+      when: always
+      allow_failure: false
+    - if: $CI_PIPELINE_SOURCE == "push" && $CI_COMMIT_TAG =~ /^br-\d+/
+      when: always
+      allow_failure: false
+    - if: $CI_COMMIT_BRANCH
+      when: manual
+      allow_failure: true
+    - when: never
+
+.rules-branch-manual-scheduled-and-test-branch-always:
+  rules:
+    - if: $CI_PIPELINE_SOURCE == "schedule"
+      when: always
+      allow_failure: false
+    - if: $CI_MERGE_REQUEST_SOURCE_BRANCH_NAME=~ /^test/
+      when: always
+      allow_failure: false
+    - if: $CI_COMMIT_BRANCH
+      when: manual
+      allow_failure: true
+    - when: never
+
+.rules-br-tag-always-branch-and-MR-manual:
+  rules:
+    - if: $CI_PIPELINE_SOURCE == 'push' && $CI_COMMIT_BRANCH
+      when: manual
+      allow_failure: true
+    - if: $CI_PIPELINE_SOURCE == 'merge_request_event'
+      when: manual
+      allow_failure: true
+    - if: $CI_PIPELINE_SOURCE == "push" && $CI_COMMIT_TAG =~ /^br-\d+/
+      when: always
+    - when: never
+

ci/setup.yml

@@ -0,0 +1,7 @@
+---
+
+include:
+  - project: 'go/bridge-internal'
+    ref: 'master'
+    file: 'ci/runners-setup.yml'
+

ci/test.yml

@@ -0,0 +1,153 @@
+
+---
+
+lint:
+  stage: test
+  extends:
+    - .image-linux-test
+    - .rules-branch-manual-br-tag-and-MR-and-devel-always
+  script:
+    - make lint
+  tags:
+    - shared-medium
+
+lint-bug-report-preview:
+  stage: test
+  extends:
+    - .image-linux-test
+    - .rules-branch-and-MR-manual
+  script:
+    - make lint-bug-report-preview
+  tags:
+    - shared-medium
+
+.script-test:
+  stage: test
+  extends:
+    - .rules-branch-manual-MR-and-devel-always
+  script:
+    - which go && go version
+    - which gcc && gcc --version
+    - make test
+  artifacts:
+    paths:
+      - coverage/**
+
+
+
+test-linux:
+  extends:
+    - .image-linux-test
+    - .script-test
+  tags:
+    - shared-large
+
+test-windows:
+  extends:
+    - .env-windows
+    - .script-test
+
+test-darwin:
+  extends:
+    - .env-darwin
+    - .script-test
+
+fuzz-linux:
+  stage: test
+  extends:
+    - .image-linux-test
+    - .rules-branch-manual-MR-and-devel-always
+  script:
+    - make fuzz
+  tags:
+    - shared-large
+
+test-linux-race:
+  extends:
+    - test-linux
+    - .rules-branch-and-MR-manual
+  script:
+    - make test-race
+
+test-integration:
+  extends:
+    - test-linux
+  script:
+    - make test-integration | tee -a integration-job.log
+  after_script:
+    - |
+      grep "Error: " integration-job.log
+  artifacts:
+    when: always
+    paths:
+      - integration-job.log
+
+test-integration-race:
+  extends:
+    - test-integration
+    - .rules-branch-and-MR-manual
+  script:
+    - make test-integration-race | tee -a integration-race-job.log
+  artifacts:
+    when: always
+    paths:
+      - integration-race-job.log
+
+
+test-integration-nightly:
+  extends:
+    - test-integration
+    - .rules-branch-manual-scheduled-and-test-branch-always
+  needs:
+    - test-integration
+  script:
+    - make test-integration-nightly | tee -a nightly-job.log
+  after_script:
+    - |
+      grep "Error: " nightly-job.log
+  artifacts:
+    when: always
+    paths:
+      - tests/result/feature-tests.xml
+      - nightly-job.log
+
+test-coverage:
+  stage: test
+  extends:
+    - .image-linux-test
+    - .rules-branch-manual-scheduled-and-test-branch-always
+  script:
+    - ./utils/coverage.sh
+  coverage: '/total:.*\(statements\).*\d+\.\d+%/'
+  needs:
+    - test-linux
+    - test-windows
+    - test-darwin
+    - test-integration
+    - test-integration-nightly
+  tags:
+    - shared-small
+  artifacts:
+    paths:
+      - coverage*
+      - coverage/**
+    when: 'always'
+    reports:
+      coverage_report:
+        coverage_format: cobertura
+        path: coverage.xml
+
+go-vuln-check:
+  extends:
+    - .image-linux-test
+    - .rules-branch-manual-MR-and-devel-always
+  stage: test
+  tags:
+    - shared-medium
+  script:
+    - ./utils/govulncheck.sh
+  artifacts:
+    when: always
+    paths:
+      - vulns*
+

cmd/Desktop-Bridge/main.go

@@ -1,4 +1,4 @@
-// Copyright (c) 2023 Proton AG
+// Copyright (c) 2025 Proton AG
 //
 // This file is part of Proton Mail Bridge.
 //
@@ -19,11 +19,17 @@ package main
 
 import (
 	"os"
+	"runtime"
 	"strings"
 
+	"github.com/ProtonMail/proton-bridge/v3/internal/constants"
+	"github.com/ProtonMail/proton-bridge/v3/internal/locations"
+	"github.com/ProtonMail/proton-bridge/v3/internal/logging"
+	"github.com/ProtonMail/proton-bridge/v3/internal/sentry"
+	"github.com/sirupsen/logrus"
+
 	"github.com/ProtonMail/proton-bridge/v3/internal/app"
 	"github.com/bradenaw/juniper/xslices"
-	"github.com/sirupsen/logrus"
 )
 
 /*
@@ -44,7 +50,72 @@ import (
 */
 
 func main() {
-	if err := app.New().Run(xslices.Filter(os.Args, func(arg string) bool { return !strings.Contains(arg, "-psn_") })); err != nil {
-		logrus.Fatal(err)
+	appErr := app.New().Run(xslices.Filter(os.Args, func(arg string) bool { return !strings.Contains(arg, "-psn_") }))
+	if appErr != nil {
+		_ = app.WithLocations(func(l *locations.Locations) error {
+			logsPath, err := l.ProvideLogsPath()
+			if err != nil {
+				return err
+			}
+
+			// Get the session ID if its specified
+			var sessionID logging.SessionID
+			if flagVal, found := getFlagValue(os.Args, app.FlagSessionID); found {
+				sessionID = logging.SessionID(flagVal)
+			} else {
+				sessionID = logging.NewSessionID()
+			}
+
+			closer, err := logging.Init(
+				logsPath,
+				sessionID,
+				logging.BridgeShortAppName,
+				logging.DefaultMaxLogFileSize,
+				logging.DefaultPruningSize,
+				"",
+			)
+			if err != nil {
+				return err
+			}
+
+			defer func() {
+				_ = logging.Close(closer)
+			}()
+
+			logrus.
+				WithField("appName", constants.FullAppName).
+				WithField("version", constants.Version).
+				WithField("revision", constants.Revision).
+				WithField("tag", constants.Tag).
+				WithField("build", constants.BuildTime).
+				WithField("runtime", runtime.GOOS).
+				WithField("args", os.Args).
+				WithField("SentryID", sentry.GetProtectedHostname()).WithError(appErr).Error("Failed to initialize bridge")
+			return nil
+		})
 	}
 }
+
+// getFlagValue - obtains the value of a specified tag
+// The flag can be of the following form `-flag value`, `--flag value`, `-flag=value` or `--flags=value`.
+func getFlagValue(argList []string, flag string) (string, bool) {
+	eqPrefix1 := "-" + flag + "="
+	eqPrefix2 := "--" + flag + "="
+
+	for i := 0; i < len(argList); i++ {
+		arg := argList[i]
+		if strings.HasPrefix(arg, eqPrefix1) {
+			val := strings.TrimPrefix(arg, eqPrefix1)
+			return val, len(val) > 0
+		}
+		if strings.HasPrefix(arg, eqPrefix2) {
+			val := strings.TrimPrefix(arg, eqPrefix2)
+			return val, len(val) > 0
+		}
+		if (arg == "-"+flag || arg == "--"+flag) && i+1 < len(argList) {
+			return argList[i+1], true
+		}
+	}
+
+	return "", false
+}

cmd/Desktop-Bridge/main_test.go

@@ -0,0 +1,47 @@
+// Copyright (c) 2025 Proton AG
+//
+// This file is part of Proton Mail Bridge.
+//
+// Proton Mail Bridge is free software: you can redistribute it and/or modify
+// it under the terms of the GNU General Public License as published by
+// the Free Software Foundation, either version 3 of the License, or
+// (at your option) any later version.
+//
+// Proton Mail Bridge is distributed in the hope that it will be useful,
+// but WITHOUT ANY WARRANTY; without even the implied warranty of
+// MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+// GNU General Public License for more details.
+//
+// You should have received a copy of the GNU General Public License
+// along with Proton Mail Bridge. If not, see <https://www.gnu.org/licenses/>.
+
+package main
+
+import (
+	"testing"
+
+	"github.com/stretchr/testify/require"
+)
+
+func TestGetFlagValue(t *testing.T) {
+	tests := []struct {
+		args     []string
+		flag     string
+		expected string
+	}{
+		{[]string{"session-id", ""}, "session-id", ""},
+		{[]string{"-session-id", ""}, "session-id", ""},
+		{[]string{"--session-id", ""}, "session-id", ""},
+		{[]string{"session-id", "test"}, "session-id", ""},
+		{[]string{"-session-id", "test"}, "session-id", "test"},
+		{[]string{"--session-id", "test"}, "session-id", "test"},
+		{[]string{"session-id=test"}, "session-id", ""},
+		{[]string{"-session-id=test"}, "session-id", "test"},
+		{[]string{"--session-id=test"}, "session-id", "test"},
+	}
+
+	for _, tt := range tests {
+		val, _ := getFlagValue(tt.args, tt.flag)
+		require.Equal(t, val, tt.expected)
+	}
+}

cmd/launcher/main.go

@@ -1,4 +1,4 @@
-// Copyright (c) 2023 Proton AG
+// Copyright (c) 2025 Proton AG
 //
 // This file is part of Proton Mail Bridge.
 //
@@ -18,13 +18,14 @@
 package main
 
 import (
-	"fmt"
+	"io"
 	"os"
 	"path/filepath"
 	"runtime"
 	"time"
 
 	"github.com/Masterminds/semver/v3"
+	"github.com/ProtonMail/gluon/async"
 	"github.com/ProtonMail/gopenpgp/v2/crypto"
 	"github.com/ProtonMail/proton-bridge/v3/internal/constants"
 	"github.com/ProtonMail/proton-bridge/v3/internal/crash"
@@ -39,6 +40,7 @@ import (
 	"github.com/elastic/go-sysinfo/types"
 	"github.com/pkg/errors"
 	"github.com/sirupsen/logrus"
+	"golang.org/x/exp/slices"
 	"golang.org/x/sys/execabs"
 )
 
@@ -46,23 +48,28 @@ const (
 	appName      = "Proton Mail Launcher"
 	exeName      = "bridge"
 	guiName      = "bridge-gui"
+	launcherName = "launcher"
 
 	FlagCLI                 = "cli"
 	FlagCLIShort            = "c"
 	FlagNonInteractive      = "noninteractive"
 	FlagNonInteractiveShort = "n"
-	FlagLauncher            = "--launcher"
-	FlagWait                = "--wait"
+	FlagLauncher            = "launcher"
+	FlagWait                = "wait"
+	FlagSessionID           = "session-id"
+	HyphenatedFlagLauncher  = "--" + FlagLauncher
+	HyphenatedFlagWait      = "--" + FlagWait
+	HyphenatedFlagSessionID = "--" + FlagSessionID
 )
 
 func main() { //nolint:funlen
 	logrus.SetLevel(logrus.DebugLevel)
 	l := logrus.WithField("launcher_version", constants.Version)
 
-	reporter := sentry.NewReporter(appName, constants.Version, useragent.New())
+	reporter := sentry.NewReporter(appName, useragent.New())
 
 	crashHandler := crash.NewHandler(reporter.ReportException)
-	defer crashHandler.HandlePanic()
+	defer async.HandlePanic(crashHandler)
 
 	locationsProvider, err := locations.NewDefaultProvider(filepath.Join(constants.VendorName, constants.ConfigName))
 	if err != nil {
@@ -75,12 +82,26 @@ func main() { //nolint:funlen
 	if err != nil {
 		l.WithError(err).Fatal("Failed to get logs path")
 	}
-	crashHandler.AddRecoveryAction(logging.DumpStackTrace(logsPath))
 
-	if err := logging.Init(logsPath, os.Getenv("VERBOSITY")); err != nil {
+	sessionID := logging.NewSessionID()
+	crashHandler.AddRecoveryAction(logging.DumpStackTrace(logsPath, sessionID, launcherName))
+
+	var closer io.Closer
+	if closer, err = logging.Init(
+		logsPath,
+		sessionID,
+		logging.LauncherShortAppName,
+		logging.DefaultMaxLogFileSize,
+		logging.NoPruning,
+		os.Getenv("VERBOSITY"),
+	); err != nil {
 		l.WithError(err).Fatal("Failed to setup logging")
 	}
 
+	defer func() {
+		_ = logging.Close(closer)
+	}()
+
 	updatesPath, err := locations.ProvideUpdatesPath()
 	if err != nil {
 		l.WithError(err).Fatal("Failed to get updates path")
@@ -107,7 +128,7 @@ func main() { //nolint:funlen
 
 	args := os.Args[1:]
 
-	exe, err := getPathToUpdatedExecutable(filepath.Base(launcher), versioner, kr, reporter)
+	exe, err := getPathToUpdatedExecutable(filepath.Base(launcher), versioner, kr)
 	if err != nil {
 		exeToLaunch := guiName
 		if inCLIMode(args) {
@@ -127,12 +148,14 @@ func main() { //nolint:funlen
 
 	l = l.WithField("exe_path", exe)
 
-	args, wait, mainExe := findAndStripWait(args)
+	args, wait, mainExes := findAndStripWait(args)
 	if wait {
+		for _, mainExe := range mainExes {
 			waitForProcessToFinish(mainExe)
 		}
+	}
 
-	cmd := execabs.Command(exe, appendLauncherPath(launcher, args)...) //nolint:gosec
+	cmd := execabs.Command(exe, appendLauncherPath(launcher, appendOrModifySessionID(args, string(sessionID)))...) //nolint:gosec
 
 	cmd.Stdin = os.Stdin
 	cmd.Stdout = os.Stdout
@@ -154,19 +177,14 @@ func main() { //nolint:funlen
 
 // appendLauncherPath add launcher path if missing.
 func appendLauncherPath(path string, args []string) []string {
-	if !sliceContains(args, FlagLauncher) {
+	if !slices.Contains(args, HyphenatedFlagLauncher) {
 		res := append([]string{}, args...)
-		res = append(res, FlagLauncher, path)
+		res = append(res, HyphenatedFlagLauncher, path)
 		return res
 	}
 	return args
 }
 
-// sliceContains checks if a value is present in a list.
-func sliceContains[T comparable](list []T, s T) bool {
-	return xslices.Any(list, func(arg T) bool { return arg == s })
-}
-
 // inCLIMode detect if CLI mode is asked.
 func inCLIMode(args []string) bool {
 	return hasFlag(args, FlagCLI) || hasFlag(args, FlagCLIShort) || hasFlag(args, FlagNonInteractive) || hasFlag(args, FlagNonInteractiveShort)
@@ -174,7 +192,12 @@ func inCLIMode(args []string) bool {
 
 // hasFlag checks if a flag is present in a list.
 func hasFlag(args []string, flag string) bool {
-	return xslices.Any(args, func(arg string) bool { return (arg == "-"+flag) || (arg == "--"+flag) })
+	return flagIndex(args, flag) >= 0
+}
+
+// flagIndex returns the position of the first occurrence of a flag int args, or -1 if the flag is not present.
+func flagIndex(args []string, flag string) int {
+	return slices.IndexFunc(args, func(arg string) bool { return (arg == "-"+flag) || (arg == "--"+flag) })
 }
 
 // findAndStrip check if a value is present in s list and remove all occurrences of the value from this list.
@@ -186,35 +209,52 @@ func findAndStrip[T comparable](slice []T, v T) (strippedList []T, found bool) {
 }
 
 // findAndStripWait Check for waiter flag get its value and clean them both.
-func findAndStripWait(args []string) ([]string, bool, string) {
+func findAndStripWait(args []string) ([]string, bool, []string) {
 	res := append([]string{}, args...)
 
 	hasFlag := false
-	var value string
-
+	values := make([]string, 0)
 	for k, v := range res {
-		if v != FlagWait {
+		if v != HyphenatedFlagWait {
 			continue
 		}
 		if k+1 >= len(res) {
 			continue
 		}
 		hasFlag = true
-		value = res[k+1]
+		values = append(values, res[k+1])
 	}
 
 	if hasFlag {
-		res, _ = findAndStrip(res, FlagWait)
-		res, _ = findAndStrip(res, value)
+		res, _ = findAndStrip(res, HyphenatedFlagWait)
+		for _, v := range values {
+			res, _ = findAndStrip(res, v)
 		}
-	return res, hasFlag, value
+	}
+	return res, hasFlag, values
+}
+
+// return args with the sessionID flag and value added or modified. The original slice is not modified.
+func appendOrModifySessionID(args []string, sessionID string) []string {
+	index := flagIndex(args, FlagSessionID)
+	if index < 0 {
+		return append(args, HyphenatedFlagSessionID, sessionID)
+	}
+
+	if index == len(args)-1 {
+		return append(args, sessionID)
+	}
+
+	res := slices.Clone(args)
+	res[index+1] = sessionID
+
+	return res
 }
 
 func getPathToUpdatedExecutable(
 	name string,
 	ver *versioner.Versioner,
 	kr *crypto.KeyRing,
-	reporter *sentry.Reporter,
 ) (string, error) {
 	versions, err := ver.ListVersions()
 	if err != nil {
@@ -236,10 +276,6 @@ func getPathToUpdatedExecutable(
 		if err := version.VerifyFiles(kr); err != nil {
 			vlog.WithError(err).Error("Files failed verification and will be removed")
 
-			if err := reporter.ReportMessage(fmt.Sprintf("version %v failed verification: %v", version, err)); err != nil {
-				vlog.WithError(err).Error("Failed to report corrupt update files")
-			}
-
 			if err := version.Remove(); err != nil {
 				vlog.WithError(err).Error("Failed to remove files")
 			}

cmd/launcher/main_test.go

@@ -1,4 +1,4 @@
-// Copyright (c) 2023 Proton AG
+// Copyright (c) 2025 Proton AG
 //
 // This file is part of Proton Mail Bridge.
 //
@@ -20,39 +20,62 @@ package main
 import (
 	"testing"
 
-	"github.com/bradenaw/juniper/xslices"
+	"github.com/ProtonMail/proton-bridge/v3/internal/logging"
 	"github.com/stretchr/testify/assert"
 )
 
-func TestSliceContains(t *testing.T) {
-	assert.True(t, sliceContains([]string{"a", "b", "c"}, "a"))
-	assert.True(t, sliceContains([]int{1, 2, 3}, 2))
-	assert.False(t, sliceContains([]string{"a", "b", "c"}, "A"))
-	assert.False(t, sliceContains([]int{1, 2, 3}, 4))
-	assert.False(t, sliceContains([]string{}, "a"))
-	assert.True(t, sliceContains([]string{"a", "a"}, "a"))
-}
-
 func TestFindAndStrip(t *testing.T) {
 	list := []string{"a", "b", "c", "c", "b", "c"}
 
 	result, found := findAndStrip(list, "a")
 	assert.True(t, found)
-	assert.True(t, xslices.Equal(result, []string{"b", "c", "c", "b", "c"}))
+	assert.Equal(t, result, []string{"b", "c", "c", "b", "c"})
 
 	result, found = findAndStrip(list, "c")
 	assert.True(t, found)
-	assert.True(t, xslices.Equal(result, []string{"a", "b", "b"}))
+	assert.Equal(t, result, []string{"a", "b", "b"})
 
 	result, found = findAndStrip([]string{"c", "c", "c"}, "c")
 	assert.True(t, found)
-	assert.True(t, xslices.Equal(result, []string{}))
+	assert.Equal(t, result, []string{})
 
 	result, found = findAndStrip(list, "A")
 	assert.False(t, found)
-	assert.True(t, xslices.Equal(result, list))
+	assert.Equal(t, result, list)
 
 	result, found = findAndStrip([]string{}, "a")
 	assert.False(t, found)
-	assert.True(t, xslices.Equal(result, []string{}))
+	assert.Equal(t, result, []string{})
+}
+
+func TestFindAndStripWait(t *testing.T) {
+	result, found, values := findAndStripWait([]string{"a", "b", "c"})
+	assert.False(t, found)
+	assert.Equal(t, result, []string{"a", "b", "c"})
+	assert.Equal(t, values, []string{})
+
+	result, found, values = findAndStripWait([]string{"a", "--wait", "b"})
+	assert.True(t, found)
+	assert.Equal(t, result, []string{"a"})
+	assert.Equal(t, values, []string{"b"})
+
+	result, found, values = findAndStripWait([]string{"a", "--wait", "b", "--wait", "c"})
+	assert.True(t, found)
+	assert.Equal(t, result, []string{"a"})
+	assert.Equal(t, values, []string{"b", "c"})
+
+	result, found, values = findAndStripWait([]string{"a", "--wait", "b", "--wait", "c", "--wait", "d"})
+	assert.True(t, found)
+	assert.Equal(t, result, []string{"a"})
+	assert.Equal(t, values, []string{"b", "c", "d"})
+}
+
+func TestAppendOrModifySessionID(t *testing.T) {
+	sessionID := string(logging.NewSessionID())
+	assert.Equal(t, appendOrModifySessionID(nil, sessionID), []string{"--session-id", sessionID})
+	assert.Equal(t, appendOrModifySessionID([]string{}, sessionID), []string{"--session-id", sessionID})
+	assert.Equal(t, appendOrModifySessionID([]string{"--cli"}, sessionID), []string{"--cli", "--session-id", sessionID})
+	assert.Equal(t, appendOrModifySessionID([]string{"--cli", "--session-id"}, sessionID), []string{"--cli", "--session-id", sessionID})
+	assert.Equal(t, appendOrModifySessionID([]string{"--cli", "--session-id"}, sessionID), []string{"--cli", "--session-id", sessionID})
+	assert.Equal(t, appendOrModifySessionID([]string{"--session-id", "<oldID>", "--cli"}, sessionID), []string{"--session-id", sessionID, "--cli"})
 }

doc/bridge.md

@@ -1,135 +0,0 @@
-# Bridge
-
-## Main blocks
-
-This is basic overview of the main bridge blocks.
-
-Note connection between IMAP/SMTP and PMAPI. IMAP and SMTP packages are in the queue to be refactored
-and we would like to try to have functionality in bridge core or bridge utilities (such as messages)
-than direct usage of PMAPI from IMAP or SMTP. Also database (BoltDB) should be moved to bridge core.
-
-```mermaid
-graph LR
-    S[Server]
-    C[Client]
-    U[User]
-
-    subgraph "Bridge app"
-        Core[Bridge core]
-        API[PMAPI]
-        Store
-        DB[BoltDB]
-        Frontend["Qt / CLI"]
-        IMAP
-        SMTP
-
-        IMAP --> Store
-        IMAP --> Core
-        SMTP --> Core
-        SMTP --> API
-        Core --> API
-        Core --> Store
-        Store --> API
-        Store --> DB
-        Frontend --> Core
-
-    end
-
-    C --> IMAP
-    C --> SMTP
-    U --> Frontend
-    API --> S
-```
-
-## Code structure
-
-More detailed graph of main types used in Bridge app and connection between them. Here is already
-communication to PMAPI only from bridge core which is not true, yet. IMAP and SMTP are still calling
-PMAPI directly.
-
-```mermaid
-graph TD
-
-    C["Client (e.g. Thunderbird)"]
-    PM[Proton Mail Server]
-
-    subgraph "Bridge app"
-        subgraph "Bridge core"
-            B[Bridge]
-            U[User]
-
-            B --> U
-        end
-
-        subgraph Store
-            StoreU[Store User]
-            StoreA[Address]
-            StoreM[Mailbox]
-
-            StoreU --> StoreA
-            StoreA --> StoreM
-        end
-
-        subgraph Credentials
-            CredStore[Store]
-            Creds[Credentials]
-
-            CredStore --> Creds
-        end
-
-        subgraph Frontend
-            CLI
-            Qt
-        end
-
-        subgraph IMAP
-            IB[IMAP backend]
-            IA[IMAP address]
-            IM[IMAP mailbox]
-
-            IB --> B
-            IB --> IA
-            IA --> IM
-            IA --> U
-            IA --> StoreA
-            IM --> StoreM
-        end
-
-        subgraph SMTP
-            SB[SMTP backend]
-            SS[SMTP session]
-
-            SB --> B
-            SB --> SS
-            SS --> U
-        end
-    end
-
-    subgraph PMAPI
-        AC[Client]
-    end
-
-    C --> IB
-    C --> SB
-
-    CLI --> B
-    Qt --> B
-
-    U --> CredStore
-    U --> Creds
-
-    U --> StoreU
-
-    StoreU --> AC
-    StoreA --> AC
-    StoreM --> AC
-
-    B --> AC
-    U --> AC
-
-    AC --> PM
-```
-
-## How to debug
-
-Run `make run-debug` which starts [Delve](https://github.com/go-delve/delve).

doc/communication.md

@@ -1,114 +0,0 @@
-# Communication
-
-## First login and sync
-
-When user logs in to the bridge for the first time, immediatelly starts the first sync.
-First sync downloads all headers of all e-mails and creates database to have proper UIDs
-and indexes for IMAP. See [database](database.md) for more information.
-
-By default, whenever it's possible, sync downloads only all e-mails maiblox which already
-have list of labels so we can construct all mailboxes (inbox, sent, trash, custom folders
-and lables) without need to download each e-mail headers many times.
-
-Note that we need to download also bodies to calculate size of the e-mail and set proper
-content type (clients uses content type for guess if e-mail contains attachment)--but only
-body, not attachment. Also it's downloaded only for the first time. After that we store
-those information in our database so next time we only sync headers, labels and so on.
-
-First sync takes some time. List of 150 messages takes about second and then we need to
-download bodies for each message. We still need to do some optimalizations. Anyway, if
-user has reasonable amount of e-mails, there is good chance user will see e-mails in the
-client right after adding account.
-
-When account is added to client, client start the sync. This sync will ask Bridge app
-for all headers (done quickly) and then starts to download all bodies and attachment.
-Unfortunatelly for some e-mail more than once if the same e-mail is in more mailboxes
-(e.g. inbox and all mail)--there is no way to tell over IMAP it's the same message.
-
-After successful login of client to IMAP, Bridge starts event loop. That periodicly ask
-servers (each 30 seconds) for new updates (new message, keys, …).
-
-```mermaid
-sequenceDiagram
-    participant S as Server
-    participant B as Bridge
-    participant C as Client
-
-    Note right of B: Set up PM account<br/>by user
-
-    loop First sync
-        B ->> S: Fetch body and attachements
-        Note right of B: Build local database<br/>(e-mail UIDs)
-    end
-
-    Note right of C: Set up IMAP/SMTP<br/>by user
-
-    C ->> B: IMAP login
-    B ->> S: Authenticate user
-    Note right of B: Create IMAP user
-
-    loop Event loop, every 30 sec
-        B ->> S: Fetch e-mail headers
-        B ->> C: Send IMAP IDLE response
-    end
-
-    C ->> B: IMAP LIST directories
-
-    loop Client sync
-        C ->> B: IMAP SELECT directory
-        C ->> B: IMAP SEARCH e-mails UIDs
-        C ->> B: IMAP FETCH of e-mail UID
-        B ->> S: Fetch body and attachements
-        Note right of B: Decrypt message<br/>and attachement
-        B ->> C: IMAP response
-    end
-```
-
-## IMAP IDLE extension
-
-IMAP IDLE is extension, it has to be supported by both client and server. IMAP server (in our case
-the bridge) supports it so clients can use it. It works by issuing `IDLE` command by the client and
-keeps the connection open. When the server has some update, server (the bridge) will respond to that
-by `EXISTS` (new message), `APPEND` (imported message), `EXPUNGE` (deleted message) or `MOVE` response.
-
-Even when there is connection with IDLE open, server can mark the client as inactive. Therefore,
-it's recommended the client should reissue the connection after each 29 minutes. This is not the
-real push and can fail!
-
-Our event loop is also simple pull and it will trigger IMAP IDLE when we get some new update from 
-the server. Would be good to have push from the server, but we need to wait for the support on API.
-
-RFC: https://tools.ietf.org/html/rfc2177
-
-```mermaid
-sequenceDiagram
-    participant S as Server
-    participant B as Bridge
-    participant C as Client
-
-    C ->> B: IMAP IDLE
-
-    loop Every 30 seconds
-        S ->> B: Checking events
-        B ->> C: IMAP response
-    end
-```
-
-## Sending e-mails
-
-E-mail are sent over standard SMTP protocol. Our bridge takes the message, encrypts and sent it
-further to our server which will then send the message to its final destination. The important
-and tricky part is encryption. See [encryption](encryption.md) or [PMEL document](https://docs.google.com/document/d/1lEBkG0DC5FOWlumInKtu4a9Cc1Eszp48ZhFy9UpPQso/edit)
-for more information.
-
-```mermaid
-sequenceDiagram
-    participant S as Server
-    participant B as Bridge
-    participant C as Client
-
-    C ->> B: SMTP send e-mail
-    Note right of B: Encrypt messages
-    B ->> S: Send encrypted e-mail
-    B ->> C: Respond OK
-```

doc/database.md

@@ -1,27 +0,0 @@
-# Database
-
-Bridge needs to have a small database to pair our IDs with IMAP UIDs and indexes. IMAP protocol
-requires every message to have an unique UID in mailbox. In this context, mailbox is not an account,
-but a folder or label. This means that one message can have more UIDs, one for each mailbox (folder), 
-and that two messages can have the same UID, but each for different mailbox (folder).
-
-IMAP index is just an index. Look at it like to an array: `["UID1", "UID2", "UID3"]`. We can access
-message by UID or index; for example index 2 and UID `UID2`. When this message is deleted, we need
-to re-index all following messages. The array will look now like `["UID1", "UID3"]` and the last
-message can be accessed by index 2 or UID `UID3`.
-
-See RFCs for more information:
-
-* https://tools.ietf.org/html/rfc822
-* https://tools.ietf.org/html/rfc3501
-
-Our database is currently built on BBolt and have those buckets (key-value storage):
-
-* Message metadata bucket:
-
-    * `[metadataBucket][API_ID] -> pmapi.Message{subject, from, to, size, other headers...}` (without body or attachment)
-
-* Mapping buckets
-
-    * `[mailboxesBucket][addressID-mailboxID][api_ids][API_ID] -> UID`
-    * `[mailboxesBucket][addressID-mailboxID][imap_ids][UID] -> API_ID`

doc/encryption.md

@@ -1,12 +0,0 @@
-# Encryption
-
-Encryption is done in PMAPI, bridge utils and bridge itself. The best would be to keep encryption
-in PMAPI and bridge utils (in package such as messages). All packages are using our high-level
-GopenPGP library on top of OpenPGP.
-
-## `gopenpgp.KeyRing`
-
-We use one `KeyRing` per address. Our usage then contains all keys for specific address. Primary
-key is always on the first position, then there old ones to be able to decrypt last e-mail.
-OpenPGP encrypts given message with all available keys, so we need to first get first (primary)
-key for encryption to have message encrypted only once with primary key.

doc/index.md

@@ -1,9 +0,0 @@
-# Bridge Documentation
-
-Documentation pages in order to read for a novice:
-
-* [Bridge code](bridge.md)
-* [Internal Bridge database](database.md)
-* [Communication between Bridge, Client and Server](communication.md)
-* [Encryption](encryption.md)
-

doc/updates.md

@@ -1,103 +0,0 @@
-# Update mechanism of Bridge
-
-There are mulitple options how to change version of application:
-* Automatic in-app update
-* Manual in-app update
-* Manual install
-
-In-app update ends with restarting bridge into new version. Automatic in-app
-update is downloading, verifying and installing the new version immediatelly
-without user confirmation. For manual in-app update user needs to confirm first.
-Update is done from special update file published on website.
-
-The manual installation requires user to download, verify and install manually
-using installer for given OS.
-
-The bridge is installed and executed differently for given OS:
-
-* Windows and Linux apps are using launcher mechanism:
-    * There is system protected installation path which is created on first
-      install. It contains bridge exe and launcher exe. When users starts
-      bridge the launcher is executed first. It will check update path compare
-      version with installed one. The newer version then is then executed.
-    * Update mechanism means to replace files in update folder which is located
-      in user space.
-
-* macOS app does not use launcher
-    * No launcher, only one executable
-    * In-App udpate replaces the bridge files in installation path directly
-
-
-```mermaid
-flowchart LR
-    subgraph Frontend
-    U[User requests<br>version check]
-    ManIns((Notify user about<br>manual install<br>is needed))
-    R((Notify user<br>about restart))
-    ManUp((Notify user about<br>manual update))
-    NF((Notify user about<br>force update))
-
-    ManUp -->|Install| InstFront[Install]
-    InstFront -->|Ok| R
-    InstFront -->|Error| ManIns
-
-    U --> CheckFront[Check online]
-    CheckFront -->|Ok| IAFront{Is new version<br>and applicable?}
-    CheckFront -->|Error| ManIns
-
-    IAFront -->|No| Latest((Notify user<br>has latest version))
-    IAFront -->|Yes| CanInstall{Can update?}
-    CanInstall -->|No| ManIns
-    CanInstall -->|Yes| NotifOrInstall{Is automatic<br>update enabled?}
-    NotifOrInstall -->|Manual| ManUp
-    end
-
-
-    subgraph Backend
-    W[Wait for next check]
-
-    W --> Check[Check online]
-
-    Check --> NV{Has new<br>version?}
-    Check -->|Error| W
-    NV -->|No new version| W
-    IA{Is install<br>applicable?}
-    NV -->|New version<br>available| IA
-    IA -->|Local rollout<br>not enough| W
-    IA -->|Yes| AU{Is automatic\nupdate enabled?}
-
-    AU -->|Yes| CanUp{Can update?}
-    CanUp -->|No| ManIns
-
-    CanUp -->|Yes| Ins[Install]
-    Ins -->|Error| ManIns
-    Ins -->|Ok| R
-
-    AU -->|No| ManUp
-    ManUp -->|Ignore| W
-
-
-    F[Force update]
-    F --> NF
-    end
-
-    ManIns --> Web[Open web page]
-    NF --> Web
-    ManUp --> Web
-    R --> Re[Restart]
-    NF --> Q[Quit bridge]
-    NotifOrInstall -->|Automatic| W
-```
-
-
-The non-trivial is to combine the update with setting change:
-* turn off/on automatic in-app updates
-* change from stable to beta or back
-
-_TODO fill flow chart details_
-
-
-We are not support downgrade functionality. Only some circumstances can lead to
-downgrading the app version.
-
-_TODO fill flow chart details_

go.mod

@@ -1,125 +1,138 @@
 module github.com/ProtonMail/proton-bridge/v3
 
-go 1.18
+go 1.23
+
+toolchain go1.23.4
 
 require (
 	github.com/0xAX/notificator v0.0.0-20220220101646-ee9b8921e557
-	github.com/Masterminds/semver/v3 v3.1.1
-	github.com/ProtonMail/gluon v0.14.2-0.20230207072331-53797c5aa3f6
+	github.com/Masterminds/semver/v3 v3.2.0
+	github.com/ProtonMail/gluon v0.17.1-0.20250116113909-2ebd96ec0bc2
 	github.com/ProtonMail/go-autostart v0.0.0-20210130080809-00ed301c8e9a
-	github.com/ProtonMail/go-proton-api v0.3.1-0.20230209110241-fe7894c4931a
-	github.com/ProtonMail/go-rfc5322 v0.11.0
-	github.com/ProtonMail/gopenpgp/v2 v2.4.10
-	github.com/PuerkitoBio/goquery v1.8.0
+	github.com/ProtonMail/go-proton-api v0.4.1-0.20250217140732-2e531f21de4c
+	github.com/ProtonMail/gopenpgp/v2 v2.8.2-proton
+	github.com/PuerkitoBio/goquery v1.8.1
 	github.com/abiosoft/ishell v2.0.0+incompatible
 	github.com/allan-simon/go-singleinstance v0.0.0-20210120080615-d0997106ab37
-	github.com/bradenaw/juniper v0.8.0
+	github.com/bradenaw/juniper v0.12.0
 	github.com/cucumber/godog v0.12.5
 	github.com/cucumber/messages-go/v16 v16.0.1
-	github.com/docker/docker-credential-helpers v0.6.3
-	github.com/elastic/go-sysinfo v1.8.1
-	github.com/emersion/go-imap v1.2.1-0.20220429085312-746087b7a317
+	github.com/docker/docker-credential-helpers v0.8.1
+	github.com/elastic/go-sysinfo v1.11.2-0.20231129083954-35e55cd2a542
+	github.com/emersion/go-imap v1.2.1
 	github.com/emersion/go-imap-id v0.0.0-20190926060100-f94a56b9ecde
 	github.com/emersion/go-message v0.16.0
 	github.com/emersion/go-sasl v0.0.0-20220912192320-0145f2c60ead
 	github.com/emersion/go-smtp v0.15.1-0.20221021114529-49b17434419d
+	github.com/emersion/go-vcard v0.0.0-20230331202150-f3d26859ccd3
 	github.com/fatih/color v1.13.0
 	github.com/getsentry/sentry-go v0.15.0
 	github.com/go-resty/resty/v2 v2.7.0
-	github.com/goccy/go-json v0.9.11
 	github.com/godbus/dbus v4.1.0+incompatible
 	github.com/golang/mock v1.6.0
-	github.com/google/go-cmp v0.5.9
+	github.com/google/go-cmp v0.6.0
 	github.com/google/uuid v1.3.0
 	github.com/hashicorp/go-multierror v1.1.1
 	github.com/jaytaylor/html2text v0.0.0-20211105163654-bc68cce691ba
+	github.com/jeandeaual/go-locale v0.0.0-20220711133428-7de61946b173
 	github.com/keybase/go-keychain v0.0.0
 	github.com/miekg/dns v1.1.50
+	github.com/pbnjay/memory v0.0.0-20210728143218-7b4eea64cf58
 	github.com/pkg/errors v0.9.1
-	github.com/pkg/profile v1.6.0
-	github.com/sirupsen/logrus v1.9.0
-	github.com/stretchr/testify v1.8.0
-	github.com/urfave/cli/v2 v2.20.3
+	github.com/pkg/profile v1.7.0
+	github.com/sirupsen/logrus v1.9.2
+	github.com/stretchr/testify v1.8.4
+	github.com/urfave/cli/v2 v2.24.4
 	github.com/vmihailenco/msgpack/v5 v5.3.5
-	go.uber.org/goleak v1.2.0
-	golang.org/x/exp v0.0.0-20221023144134-a1e5550cf13e
-	golang.org/x/net v0.1.0
-	golang.org/x/sys v0.1.0
-	golang.org/x/text v0.4.0
-	google.golang.org/grpc v1.50.1
-	google.golang.org/protobuf v1.28.1
+	go.uber.org/goleak v1.2.1
+	golang.org/x/exp v0.0.0-20230522175609-2e198f4a06a1
+	golang.org/x/net v0.34.0
+	golang.org/x/oauth2 v0.7.0
+	golang.org/x/sys v0.29.0
+	golang.org/x/text v0.21.0
+	google.golang.org/api v0.114.0
+	google.golang.org/grpc v1.56.3
+	google.golang.org/protobuf v1.33.0
 	howett.net/plist v1.0.0
 )
 
 require (
-	ariga.io/atlas v0.7.0 // indirect
-	entgo.io/ent v0.11.2 // indirect
+	cloud.google.com/go/compute v1.19.1 // indirect
+	cloud.google.com/go/compute/metadata v0.2.3 // indirect
 	github.com/ProtonMail/bcrypt v0.0.0-20211005172633-e235017c1baf // indirect
-	github.com/ProtonMail/go-crypto v0.0.0-20220824120805-4b6e5c587895 // indirect
-	github.com/ProtonMail/go-mime v0.0.0-20220429130430-2192574d760f // indirect
-	github.com/ProtonMail/go-srp v0.0.5 // indirect
+	github.com/ProtonMail/go-crypto v1.1.4-proton // indirect
+	github.com/ProtonMail/go-mime v0.0.0-20230322103455-7d82a3887f2f // indirect
+	github.com/ProtonMail/go-srp v0.0.7 // indirect
 	github.com/abiosoft/readline v0.0.0-20180607040430-155bce2042db // indirect
-	github.com/agext/levenshtein v1.2.3 // indirect
-	github.com/andybalholm/cascadia v1.3.1 // indirect
-	github.com/antlr/antlr4/runtime/Go/antlr v1.4.10 // indirect
-	github.com/apparentlymart/go-textseg/v13 v13.0.0 // indirect
+	github.com/andybalholm/cascadia v1.3.2 // indirect
+	github.com/bytedance/sonic v1.9.1 // indirect
+	github.com/chenzhuoyu/base64x v0.0.0-20221115062448-fe3a3abad311 // indirect
 	github.com/chzyer/test v1.0.0 // indirect
-	github.com/cloudflare/circl v1.2.0 // indirect
+	github.com/cloudflare/circl v1.5.0 // indirect
 	github.com/cpuguy83/go-md2man/v2 v2.0.2 // indirect
 	github.com/cronokirby/saferith v0.33.0 // indirect
 	github.com/cucumber/gherkin-go/v19 v19.0.3 // indirect
-	github.com/danieljoos/wincred v1.1.2 // indirect
+	github.com/danieljoos/wincred v1.2.1 // indirect
 	github.com/davecgh/go-spew v1.1.1 // indirect
 	github.com/elastic/go-windows v1.0.1 // indirect
 	github.com/emersion/go-textwrapper v0.0.0-20200911093747-65d896831594 // indirect
-	github.com/emersion/go-vcard v0.0.0-20220507122617-d4056df0ec4a // indirect
+	github.com/felixge/fgprof v0.9.3 // indirect
 	github.com/flynn-archive/go-shlex v0.0.0-20150515145356-3f9db97f8568 // indirect
+	github.com/gabriel-vasile/mimetype v1.4.2 // indirect
 	github.com/gin-contrib/sse v0.1.0 // indirect
-	github.com/gin-gonic/gin v1.8.1 // indirect
-	github.com/go-openapi/inflect v0.19.0 // indirect
-	github.com/go-playground/locales v0.14.0 // indirect
-	github.com/go-playground/universal-translator v0.18.0 // indirect
-	github.com/go-playground/validator/v10 v10.11.1 // indirect
+	github.com/gin-gonic/gin v1.9.1 // indirect
+	github.com/go-playground/locales v0.14.1 // indirect
+	github.com/go-playground/universal-translator v0.18.1 // indirect
+	github.com/go-playground/validator/v10 v10.14.0 // indirect
+	github.com/goccy/go-json v0.10.2 // indirect
 	github.com/gofrs/uuid v4.3.0+incompatible // indirect
-	github.com/golang/protobuf v1.5.2 // indirect
+	github.com/golang/groupcache v0.0.0-20200121045136-8c9f03a8e57e // indirect
+	github.com/golang/protobuf v1.5.3 // indirect
+	github.com/google/pprof v0.0.0-20211214055906-6f57359322fd // indirect
+	github.com/googleapis/enterprise-certificate-proxy v0.2.3 // indirect
+	github.com/googleapis/gax-go/v2 v2.7.1 // indirect
 	github.com/hashicorp/errwrap v1.1.0 // indirect
 	github.com/hashicorp/go-immutable-radix v1.3.1 // indirect
 	github.com/hashicorp/go-memdb v1.3.3 // indirect
 	github.com/hashicorp/golang-lru v0.5.4 // indirect
-	github.com/hashicorp/hcl/v2 v2.14.0 // indirect
 	github.com/joeshaw/multierror v0.0.0-20140124173710-69b34d4ec901 // indirect
 	github.com/json-iterator/go v1.1.12 // indirect
-	github.com/leodido/go-urn v1.2.1 // indirect
+	github.com/klauspost/cpuid/v2 v2.2.4 // indirect
+	github.com/leodido/go-urn v1.2.4 // indirect
 	github.com/mattn/go-colorable v0.1.13 // indirect
-	github.com/mattn/go-isatty v0.0.16 // indirect
+	github.com/mattn/go-isatty v0.0.19 // indirect
 	github.com/mattn/go-runewidth v0.0.14 // indirect
-	github.com/mattn/go-sqlite3 v1.14.15 // indirect
-	github.com/mitchellh/go-wordwrap v1.0.1 // indirect
+	github.com/mattn/go-sqlite3 v1.14.22 // indirect
 	github.com/modern-go/concurrent v0.0.0-20180306012644-bacd9c7ef1dd // indirect
 	github.com/modern-go/reflect2 v1.0.2 // indirect
 	github.com/olekukonko/tablewriter v0.0.5 // indirect
-	github.com/pelletier/go-toml/v2 v2.0.5 // indirect
+	github.com/pelletier/go-toml/v2 v2.0.8 // indirect
+	github.com/pierrec/lz4/v4 v4.1.17 // indirect
 	github.com/pmezard/go-difflib v1.0.0 // indirect
-	github.com/prometheus/procfs v0.8.0 // indirect
+	github.com/prometheus/procfs v0.12.0 // indirect
 	github.com/rivo/uniseg v0.4.2 // indirect
 	github.com/russross/blackfriday/v2 v2.1.0 // indirect
 	github.com/spf13/pflag v1.0.5 // indirect
 	github.com/ssor/bom v0.0.0-20170718123548-6386211fdfcf // indirect
-	github.com/ugorji/go/codec v1.2.7 // indirect
+	github.com/twitchyliquid64/golang-asm v0.15.1 // indirect
+	github.com/ugorji/go/codec v1.2.11 // indirect
 	github.com/vmihailenco/tagparser/v2 v2.0.0 // indirect
 	github.com/xrash/smetrics v0.0.0-20201216005158-039620a65673 // indirect
-	github.com/zclconf/go-cty v1.11.0 // indirect
-	golang.org/x/crypto v0.1.0 // indirect
-	golang.org/x/mod v0.6.0-dev.0.20220419223038-86c51ed26bb4 // indirect
-	golang.org/x/sync v0.0.0-20220907140024-f12130a52804 // indirect
-	golang.org/x/tools v0.1.13-0.20220804200503-81c7dc4e4efa // indirect
-	google.golang.org/genproto v0.0.0-20220921223823-23cae91e6737 // indirect
-	gopkg.in/yaml.v2 v2.4.0 // indirect
+	gitlab.com/c0b/go-ordered-json v0.0.0-20201030195603-febf46534d5a // indirect
+	go.opencensus.io v0.24.0 // indirect
+	golang.org/x/arch v0.3.0 // indirect
+	golang.org/x/crypto v0.32.0 // indirect
+	golang.org/x/mod v0.17.0 // indirect
+	golang.org/x/sync v0.10.0 // indirect
+	golang.org/x/tools v0.21.1-0.20240508182429-e35e4ccd0d2d // indirect
+	google.golang.org/appengine v1.6.7 // indirect
+	google.golang.org/genproto v0.0.0-20230410155749-daa745c078e1 // indirect
 	gopkg.in/yaml.v3 v3.0.1 // indirect
 )
 
 replace (
-	github.com/docker/docker-credential-helpers => github.com/ProtonMail/docker-credential-helpers v1.1.0
-	github.com/emersion/go-message => github.com/ProtonMail/go-message v0.0.0-20210611055058-fabeff2ec753
-	github.com/keybase/go-keychain => github.com/cuthix/go-keychain v0.0.0-20220405075754-31e7cee908fe
+	github.com/emersion/go-message => github.com/ProtonMail/go-message v0.13.1-0.20240919135104-3bc88e6a9423
+	github.com/emersion/go-smtp => github.com/ProtonMail/go-smtp v0.0.0-20231109081432-2b3d50599865
+	github.com/go-resty/resty/v2 => github.com/LBeernaertProton/resty/v2 v2.0.0-20231129100320-dddf8030d93a
+	github.com/keybase/go-keychain => github.com/cuthix/go-keychain v0.0.0-20240103134243-0b6a41580b77
 )

go.sum

@@ -1,5 +1,3 @@
-ariga.io/atlas v0.7.0 h1:daEFdUsyNm7EHyzcMfjWwq/fVv48fCfad+dIGyobY1k=
-ariga.io/atlas v0.7.0/go.mod h1:ft47uSh5hWGDCmQC9DsztZg6Xk+KagM5Ts/mZYKb9JE=
 cloud.google.com/go v0.26.0/go.mod h1:aQUYkXzVsufM+DwF1aE+0xfcU+56JwCaLick0ClmMTw=
 cloud.google.com/go v0.34.0/go.mod h1:aQUYkXzVsufM+DwF1aE+0xfcU+56JwCaLick0ClmMTw=
 cloud.google.com/go v0.38.0/go.mod h1:990N+gfupTy94rShfmMCWGDn0LpTmnzTp2qbd1dvSRU=
@@ -7,67 +5,70 @@ cloud.google.com/go v0.44.1/go.mod h1:iSa0KzasP4Uvy3f1mN/7PiObzGgflwredwwASm/v6A
 cloud.google.com/go v0.44.2/go.mod h1:60680Gw3Yr4ikxnPRS/oxxkBccT6SA1yMk63TGekxKY=
 cloud.google.com/go v0.45.1/go.mod h1:RpBamKRgapWJb87xiFSdk4g1CME7QZg3uwTez+TSTjc=
 cloud.google.com/go v0.46.3/go.mod h1:a6bKKbmY7er1mI7TEI4lsAkts/mkhTSZK8w33B4RAg0=
+cloud.google.com/go v0.110.0 h1:Zc8gqp3+a9/Eyph2KDmcGaPtbKRIoqq4YTlL4NMD0Ys=
 cloud.google.com/go/bigquery v1.0.1/go.mod h1:i/xbL2UlR5RvWAURpBYZTtm/cXjCha9lbfbpx4poX+o=
+cloud.google.com/go/compute v1.19.1 h1:am86mquDUgjGNWxiGn+5PGLbmgiWXlE/yNWpIpNvuXY=
+cloud.google.com/go/compute v1.19.1/go.mod h1:6ylj3a05WF8leseCdIf77NK0g1ey+nj5IKd5/kvShxE=
+cloud.google.com/go/compute/metadata v0.2.3 h1:mg4jlk7mCAj6xXp9UJ4fjI9VUI5rubuGBW5aJ7UnBMY=
+cloud.google.com/go/compute/metadata v0.2.3/go.mod h1:VAV5nSsACxMJvgaAuX6Pk2AawlZn8kiOGuCv6gTkwuA=
 cloud.google.com/go/datastore v1.0.0/go.mod h1:LXYbyblFSglQ5pkeyhO+Qmw7ukd3C+pD7TKLgZqpHYE=
 cloud.google.com/go/firestore v1.1.0/go.mod h1:ulACoGHTpvq5r8rxGJ4ddJZBZqakUQqClKRT5SZwBmk=
+cloud.google.com/go/longrunning v0.4.1 h1:v+yFJOfKC3yZdY6ZUI933pIYdhyhV8S3NpWrXWmg7jM=
+cloud.google.com/go/longrunning v0.4.1/go.mod h1:4iWDqhBZ70CvZ6BfETbvam3T8FMvLK+eFj0E6AaRQTo=
 cloud.google.com/go/pubsub v1.0.1/go.mod h1:R0Gpsv3s54REJCy4fxDixWD93lHJMoZTyQ2kNxGRt3I=
 cloud.google.com/go/storage v1.0.0/go.mod h1:IhtSnM/ZTZV8YYJWCY8RULGVqBDmpoyjwiyrjsg+URw=
 dmitri.shuralyov.com/gpu/mtl v0.0.0-20190408044501-666a987793e9/go.mod h1:H6x//7gZCb22OMCxBHrMx7a5I7Hp++hsVxbQ4BYO7hU=
-entgo.io/ent v0.11.2 h1:UM2/BUhF2FfsxPHRxLjQbhqJNaDdVlOwNIAMLs2jyto=
-entgo.io/ent v0.11.2/go.mod h1:YGHEQnmmIUgtD5b1ICD5vg74dS3npkNnmC5K+0J+IHU=
+fyne.io/fyne v1.4.2/go.mod h1:xL4c3WmpE/Tvz5CEm5vqsaizU/EeOCm9DYlL2GtTSiM=
 github.com/0xAX/notificator v0.0.0-20220220101646-ee9b8921e557 h1:l6surSnJ3RP4qA1qmKJ+hQn3UjytosdoG27WGjrDlVs=
 github.com/0xAX/notificator v0.0.0-20220220101646-ee9b8921e557/go.mod h1:sTrmvD/TxuypdOERsDOS7SndZg0rzzcCi1b6wQMXUYM=
 github.com/BurntSushi/toml v0.3.1/go.mod h1:xHWCNGjB5oqiDr8zfno3MHue2Ht5sIBksp03qcyfWMU=
 github.com/BurntSushi/xgb v0.0.0-20160522181843-27f122750802/go.mod h1:IVnqGOEym/WlBOVXweHU+Q+/VP0lqqI8lqeDx9IjBqo=
-github.com/DATA-DOG/go-sqlmock v1.5.0 h1:Shsta01QNfFxHCfpW6YH2STWB0MudeXXEWMr20OEh60=
-github.com/Masterminds/semver/v3 v3.1.1 h1:hLg3sBzpNErnxhQtUy/mmLR2I9foDujNK030IGemrRc=
-github.com/Masterminds/semver/v3 v3.1.1/go.mod h1:VPu/7SZ7ePZ3QOrcuXROw5FAcLl4a0cBrbBpGY/8hQs=
+github.com/Kodeworks/golang-image-ico v0.0.0-20141118225523-73f0f4cfade9/go.mod h1:7uhhqiBaR4CpN0k9rMjOtjpcfGd6DG2m04zQxKnWQ0I=
+github.com/LBeernaertProton/resty/v2 v2.0.0-20231129100320-dddf8030d93a h1:eQO/GF/+H8/9udc9QAgieFr+jr1tjXlJo35RAhsUbWY=
+github.com/LBeernaertProton/resty/v2 v2.0.0-20231129100320-dddf8030d93a/go.mod h1:iiP/OpA0CkcL3IGt1O0+/SIItFUbkkyw5BGXiVdTu+A=
+github.com/Masterminds/semver/v3 v3.2.0 h1:3MEsd0SM6jqZojhjLWWeBY+Kcjy9i6MQAeY7YgDP83g=
+github.com/Masterminds/semver/v3 v3.2.0/go.mod h1:qvl/7zhW3nngYb5+80sSMF+FG2BjYrf8m9wsX0PNOMQ=
+github.com/Microsoft/go-winio v0.6.0 h1:slsWYD/zyx7lCXoZVlvQrj0hPTM1HI4+v1sIda2yDvg=
+github.com/Microsoft/go-winio v0.6.0/go.mod h1:cTAf44im0RAYeL23bpB+fzCyDH2MJiz2BO69KH/soAE=
 github.com/OneOfOne/xxhash v1.2.2/go.mod h1:HSdplMjZKSmBqAxg5vPj2TmRDmfkzw+cTzAElWljhcU=
 github.com/ProtonMail/bcrypt v0.0.0-20210511135022-227b4adcab57/go.mod h1:HecWFHognK8GfRDGnFQbW/LiV7A3MX3gZVs45vk5h8I=
 github.com/ProtonMail/bcrypt v0.0.0-20211005172633-e235017c1baf h1:yc9daCCYUefEs69zUkSzubzjBbL+cmOXgnmt9Fyd9ug=
 github.com/ProtonMail/bcrypt v0.0.0-20211005172633-e235017c1baf/go.mod h1:o0ESU9p83twszAU8LBeJKFAAMX14tISa0yk4Oo5TOqo=
-github.com/ProtonMail/docker-credential-helpers v1.1.0 h1:+kvUIpwWcbtP3WFv5sSvkFn/XLzSqPOB5AAthuk9xPk=
-github.com/ProtonMail/docker-credential-helpers v1.1.0/go.mod h1:mK0aBveCxhnQ756AmaTfXMZDeULvheYVhF/MWMErN5g=
-github.com/ProtonMail/gluon v0.14.2-0.20230207072331-53797c5aa3f6 h1:HR944ZH7lN6sCA9OJMTdyoH1IRU0dBjxQHc7W0vFVrg=
-github.com/ProtonMail/gluon v0.14.2-0.20230207072331-53797c5aa3f6/go.mod h1:z2AxLIiBCT1K+0OBHyaDI7AEaO5qI6/BEC2TE42vs4Q=
+github.com/ProtonMail/gluon v0.17.1-0.20250116113909-2ebd96ec0bc2 h1:lDgMidI/9j2eedavcy7YICv8+F73ooVTUoUGBE4dO0s=
+github.com/ProtonMail/gluon v0.17.1-0.20250116113909-2ebd96ec0bc2/go.mod h1:0/c03TzZPNiSgY5UDJK1iRDkjlDPwWugxTT6et2qDu8=
 github.com/ProtonMail/go-autostart v0.0.0-20210130080809-00ed301c8e9a h1:D+aZah+k14Gn6kmL7eKxoo/4Dr/lK3ChBcwce2+SQP4=
 github.com/ProtonMail/go-autostart v0.0.0-20210130080809-00ed301c8e9a/go.mod h1:oTGdE7/DlWIr23G0IKW3OXK9wZ5Hw1GGiaJFccTvZi4=
-github.com/ProtonMail/go-crypto v0.0.0-20210428141323-04723f9f07d7/go.mod h1:z4/9nQmJSSwwds7ejkxaJwO37dru3geImFUdJlaLzQo=
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@@ -297,8 +354,6 @@ github.com/mitchellh/cli v1.0.0/go.mod h1:hNIlj7HEI86fIcpObd7a0FcrxTWetlwJDGcceT
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@@ -372,28 +436,35 @@ github.com/spf13/pflag v1.0.3/go.mod h1:DYY7MBk1bdzusC3SYhjObp+wFpr4gzcvqqNjLnIn
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@@ -560,10 +676,14 @@ google.golang.org/api v0.7.0/go.mod h1:WtwebWUNSVBH/HAw79HIFXZNqEvBhG+Ra+ax0hx3E
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@@ -573,20 +693,35 @@ google.golang.org/genproto v0.0.0-20190801165951-fa694d86fc64/go.mod h1:DMBHOl98
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 gopkg.in/check.v1 v1.0.0-20201130134442-10cb98267c6c/go.mod h1:JHkPIbrfpd72SG/EVd6muEfDQjcINNoR0C8j2r3qZ4Q=
 gopkg.in/errgo.v2 v2.1.0/go.mod h1:hNsd1EY+bozCKY1Ytp96fpM3vjJbqLJn88ws8XvfDNI=
@@ -598,17 +733,17 @@ gopkg.in/yaml.v2 v2.2.1/go.mod h1:hI93XBmqTisBFMUTm0b8Fm+jr3Dg1NNxqwp+5A1VGuI=
 gopkg.in/yaml.v2 v2.2.2/go.mod h1:hI93XBmqTisBFMUTm0b8Fm+jr3Dg1NNxqwp+5A1VGuI=
 gopkg.in/yaml.v2 v2.2.4/go.mod h1:hI93XBmqTisBFMUTm0b8Fm+jr3Dg1NNxqwp+5A1VGuI=
 gopkg.in/yaml.v2 v2.2.8/go.mod h1:hI93XBmqTisBFMUTm0b8Fm+jr3Dg1NNxqwp+5A1VGuI=
-gopkg.in/yaml.v2 v2.4.0 h1:D8xgwECY7CYvx+Y2n4sBz93Jn9JRvxdiyyo8CTfuKaY=
-gopkg.in/yaml.v2 v2.4.0/go.mod h1:RDklbk79AGWmwhnvt/jBztapEOGDOx6ZbXqjP6csGnQ=
+gopkg.in/yaml.v2 v2.3.0/go.mod h1:hI93XBmqTisBFMUTm0b8Fm+jr3Dg1NNxqwp+5A1VGuI=
 gopkg.in/yaml.v3 v3.0.0-20200313102051-9f266ea9e77c/go.mod h1:K4uyk7z7BCEPqu6E+C64Yfv1cQ7kz7rIZviUmN+EgEM=
 gopkg.in/yaml.v3 v3.0.0-20200615113413-eeeca48fe776/go.mod h1:K4uyk7z7BCEPqu6E+C64Yfv1cQ7kz7rIZviUmN+EgEM=
-gopkg.in/yaml.v3 v3.0.0-20210107192922-496545a6307b/go.mod h1:K4uyk7z7BCEPqu6E+C64Yfv1cQ7kz7rIZviUmN+EgEM=
 gopkg.in/yaml.v3 v3.0.1 h1:fxVm/GzAzEWqLHuvctI91KS9hhNmmWOoWu0XTYJS7CA=
 gopkg.in/yaml.v3 v3.0.1/go.mod h1:K4uyk7z7BCEPqu6E+C64Yfv1cQ7kz7rIZviUmN+EgEM=
 honnef.co/go/tools v0.0.0-20190102054323-c2f93a96b099/go.mod h1:rf3lG4BRIbNafJWhAfAdb/ePZxsR/4RtNHQocxwk9r4=
 honnef.co/go/tools v0.0.0-20190106161140-3f1c8253044a/go.mod h1:rf3lG4BRIbNafJWhAfAdb/ePZxsR/4RtNHQocxwk9r4=
 honnef.co/go/tools v0.0.0-20190418001031-e561f6794a2a/go.mod h1:rf3lG4BRIbNafJWhAfAdb/ePZxsR/4RtNHQocxwk9r4=
+honnef.co/go/tools v0.0.0-20190523083050-ea95bdfd59fc/go.mod h1:rf3lG4BRIbNafJWhAfAdb/ePZxsR/4RtNHQocxwk9r4=
 honnef.co/go/tools v0.0.1-2019.2.3/go.mod h1:a3bituU0lyd329TUQxRnasdCoJDkEUEAqEt0JzvZhAg=
 howett.net/plist v1.0.0 h1:7CrbWYbPPO/PyNy38b2EB/+gYbjCe2DXBxgtOOZbSQM=
 howett.net/plist v1.0.0/go.mod h1:lqaXoTrLY4hg8tnEzNru53gicrbv7rrk+2xJA/7hw9g=
 rsc.io/binaryregexp v0.2.0/go.mod h1:qTv7/COck+e2FymRvadv62gMdZztPaShugOCi3I+8D8=
+rsc.io/pdf v0.1.1/go.mod h1:n8OzWcQ6Sp37PL01nO98y4iUCRdTGarVfzxY20ICaU4=

internal/app/app.go

@@ -1,4 +1,4 @@
-// Copyright (c) 2023 Proton AG
+// Copyright (c) 2025 Proton AG
 //
 // This file is part of Proton Mail Bridge.
 //
@@ -19,27 +19,32 @@ package app
 
 import (
 	"fmt"
-	"math/rand"
+	"io"
 	"net/http"
 	"net/http/cookiejar"
+	"net/url"
 	"os"
 	"path/filepath"
 	"runtime"
 	"time"
 
 	"github.com/Masterminds/semver/v3"
+	"github.com/ProtonMail/gluon/async"
 	"github.com/ProtonMail/proton-bridge/v3/internal/bridge"
 	"github.com/ProtonMail/proton-bridge/v3/internal/constants"
 	"github.com/ProtonMail/proton-bridge/v3/internal/cookies"
 	"github.com/ProtonMail/proton-bridge/v3/internal/crash"
 	"github.com/ProtonMail/proton-bridge/v3/internal/events"
 	"github.com/ProtonMail/proton-bridge/v3/internal/focus"
+	"github.com/ProtonMail/proton-bridge/v3/internal/frontend/theme"
 	"github.com/ProtonMail/proton-bridge/v3/internal/locations"
 	"github.com/ProtonMail/proton-bridge/v3/internal/logging"
 	"github.com/ProtonMail/proton-bridge/v3/internal/sentry"
 	"github.com/ProtonMail/proton-bridge/v3/internal/useragent"
 	"github.com/ProtonMail/proton-bridge/v3/internal/vault"
+	"github.com/ProtonMail/proton-bridge/v3/pkg/keychain"
 	"github.com/ProtonMail/proton-bridge/v3/pkg/restarter"
+	"github.com/elastic/go-sysinfo"
 	"github.com/pkg/profile"
 	"github.com/sirupsen/logrus"
 	"github.com/urfave/cli/v2"
@@ -50,6 +55,9 @@ const (
 	flagCPUProfile      = "cpu-prof"
 	flagCPUProfileShort = "p"
 
+	flagTraceProfile      = "trace-prof"
+	flagTraceProfileShort = "t"
+
 	flagMemProfile      = "mem-prof"
 	flagMemProfileShort = "m"
 
@@ -67,6 +75,13 @@ const (
 
 	flagLogIMAP = "log-imap"
 	flagLogSMTP = "log-smtp"
+
+	flagEnableKeychainTest  = "enable-keychain-test"
+	flagDisableKeychainTest = "disable-keychain-test"
+
+	flagSoftwareRenderer    = "software-renderer"
+	flagSetSoftwareRenderer = "set-software-renderer"
+	flagSetHardwareRenderer = "set-hardware-renderer"
 )
 
 // Hidden flags.
@@ -74,14 +89,32 @@ const (
 	flagLauncher  = "launcher"
 	flagNoWindow  = "no-window"
 	flagParentPID = "parent-pid"
-	flagSoftwareRenderer = "software-renderer"
+	FlagSessionID = "session-id"
 )
 
 const (
 	appUsage     = "Proton Mail IMAP and SMTP Bridge"
+	appShortName = "bridge"
 )
 
-func New() *cli.App { //nolint:funlen
+// the two flags below have been deprecated by BRIDGE-281. We however keep them so that bridge does not error if they are passed on startup.
+var cliFlagEnableKeychainTest = &cli.BoolFlag{ //nolint:gochecknoglobals
+	Name:               flagEnableKeychainTest,
+	Usage:              "This flag is deprecated and does nothing",
+	Value:              false,
+	DisableDefaultText: true,
+	Hidden:             true,
+}
+
+var cliFlagDisableKeychainTest = &cli.BoolFlag{ //nolint:gochecknoglobals
+	Name:               flagDisableKeychainTest,
+	Usage:              "This flag is deprecated and does nothing",
+	Value:              false,
+	DisableDefaultText: true,
+	Hidden:             true,
+}
+
+func New() *cli.App {
 	app := cli.NewApp()
 
 	app.Name = constants.FullAppName
@@ -92,6 +125,11 @@ func New() *cli.App { //nolint:funlen
 			Aliases: []string{flagCPUProfileShort},
 			Usage:   "Generate CPU profile",
 		},
+		&cli.BoolFlag{
+			Name:    flagTraceProfile,
+			Aliases: []string{flagTraceProfileShort},
+			Usage:   "Generate Trace profile",
+		},
 		&cli.BoolFlag{
 			Name:    flagMemProfile,
 			Aliases: []string{flagMemProfileShort},
@@ -125,6 +163,24 @@ func New() *cli.App { //nolint:funlen
 			Name:  flagLogSMTP,
 			Usage: "Enable logging of SMTP communications (may contain decrypted data!)",
 		},
+		&cli.BoolFlag{
+			Name:               flagSoftwareRenderer, // This flag is ignored by bridge, but should be passed to launcher in case of restart, so it need to be accepted by the CLI parser.
+			Usage:              "Use software rendering of the GUI for the current execution of the application",
+			Value:              false,
+			DisableDefaultText: true,
+		},
+		&cli.BoolFlag{
+			Name:               flagSetSoftwareRenderer, // This flag is ignored by bridge, we just want it to be shown in the help (BRIDGE-217).
+			Usage:              "Toggle software rendering of the GUI for the current and future executions of the application",
+			Value:              false,
+			DisableDefaultText: true,
+		},
+		&cli.BoolFlag{
+			Name:               flagSetHardwareRenderer, // This flag is ignored by bridge, we just want it to be shown in the help (BRIDGE-217).
+			Usage:              "Toggle hardware rendering of the GUI for the current and future executions of the application",
+			Value:              false,
+			DisableDefaultText: true,
+		},
 
 		// Hidden flags
 		&cli.BoolFlag{
@@ -143,23 +199,32 @@ func New() *cli.App { //nolint:funlen
 			Hidden: true,
 			Value:  -1,
 		},
-		&cli.BoolFlag{
-			Name:   flagSoftwareRenderer, // This flag is ignored by bridge, but should be passed to launcher in case of restart, so it need to be accepted by the CLI parser.
-			Usage:  "GUI is using software renderer",
+		&cli.StringFlag{
+			Name:   FlagSessionID,
 			Hidden: true,
-			Value:  false,
 		},
 	}
 
+	// We override the default help value because we want "Show" to be capitalized
+	cli.HelpFlag = &cli.BoolFlag{
+		Name:               "help",
+		Aliases:            []string{"h"},
+		Usage:              "Show help",
+		DisableDefaultText: true,
+	}
+
+	if onMacOS() {
+		// The two flags below were introduced for BRIDGE-116, and are available only on macOS.
+		// They have been later removed fro BRIDGE-281.
+		app.Flags = append(app.Flags, cliFlagEnableKeychainTest, cliFlagDisableKeychainTest)
+	}
+
 	app.Action = run
 
 	return app
 }
 
-func run(c *cli.Context) error { //nolint:funlen
-	// Seed the default RNG from the math/rand package.
-	rand.Seed(time.Now().UnixNano())
-
+func run(c *cli.Context) error {
 	// Get the current bridge version.
 	version, err := semver.NewVersion(constants.Version)
 	if err != nil {
@@ -170,7 +235,7 @@ func run(c *cli.Context) error { //nolint:funlen
 	identifier := useragent.New()
 
 	// Create a new Sentry client that will be used to report crashes etc.
-	reporter := sentry.NewReporter(constants.FullAppName, constants.Version, identifier)
+	reporter := sentry.NewReporter(constants.FullAppName, identifier)
 
 	// Determine the exe that should be used to restart/autostart the app.
 	// By default, this is the launcher, if used. Otherwise, we try to get
@@ -185,14 +250,19 @@ func run(c *cli.Context) error { //nolint:funlen
 		exe = os.Args[0]
 	}
 
+	var logCloser io.Closer
+	defer func() {
+		_ = logging.Close(logCloser)
+	}()
+
+	// Restart the app if requested.
+	err = withRestarter(exe, func(restarter *restarter.Restarter) error {
+		// Handle crashes with various actions.
+		return withCrashHandler(restarter, reporter, func(crashHandler *crash.Handler, quitCh <-chan struct{}) error {
 			migrationErr := migrateOldVersions()
 
 			// Run with profiling if requested.
 			return withProfiler(c, func() error {
-		// Restart the app if requested.
-		return withRestarter(exe, func(restarter *restarter.Restarter) error {
-			// Handle crashes with various actions.
-			return withCrashHandler(restarter, reporter, func(crashHandler *crash.Handler, quitCh <-chan struct{}) error {
 				// Load the locations where we store our files.
 				return WithLocations(func(locations *locations.Locations) error {
 					// Migrate the keychain helper.
@@ -201,47 +271,55 @@ func run(c *cli.Context) error { //nolint:funlen
 					}
 
 					// Initialize logging.
-					return withLogging(c, crashHandler, locations, func() error {
+					return withLogging(c, crashHandler, locations, func(closer io.Closer) error {
+						logCloser = closer
+
 						// If there was an error during migration, log it now.
 						if migrationErr != nil {
 							logrus.WithError(migrationErr).Error("Failed to migrate old app data")
 						}
 
 						// Ensure we are the only instance running.
-						return withSingleInstance(locations, version, func() error {
+						settings, err := locations.ProvideSettingsPath()
+						if err != nil {
+							logrus.WithError(err).Error("Failed to get settings path")
+						}
+
+						return withSingleInstance(settings, locations.GetLockFile(), version, func() error {
+							// Look for available keychains
+							return WithKeychainList(crashHandler, func(keychains *keychain.List) error {
 								// Unlock the encrypted vault.
-							return WithVault(locations, func(vault *vault.Vault, insecure, corrupt bool) error {
-								// Report insecure vault.
-								if insecure {
-									_ = reporter.ReportMessageWithContext("Vault is insecure", map[string]interface{}{})
-								}
-
-								// Report corrupt vault.
-								if corrupt {
-									_ = reporter.ReportMessageWithContext("Vault is corrupt", map[string]interface{}{})
-								}
-
-								if !vault.Migrated() {
+								return WithVault(reporter, locations, keychains, crashHandler, func(v *vault.Vault, insecure, corrupt bool) error {
+									if !v.Migrated() {
 										// Migrate old settings into the vault.
-									if err := migrateOldSettings(vault); err != nil {
+										if err := migrateOldSettings(v); err != nil {
 											logrus.WithError(err).Error("Failed to migrate old settings")
 										}
 
 										// Migrate old accounts into the vault.
-									if err := migrateOldAccounts(locations, vault); err != nil {
+										if err := migrateOldAccounts(locations, keychains, v); err != nil {
 											logrus.WithError(err).Error("Failed to migrate old accounts")
 										}
 
 										// The vault has been migrated.
-									if err := vault.SetMigrated(); err != nil {
+										if err := v.SetMigrated(); err != nil {
 											logrus.WithError(err).Error("Failed to mark vault as migrated")
 										}
 									}
 
+									logrus.WithFields(logrus.Fields{
+										"lastVersion": v.GetLastVersion().String(),
+										"showAllMail": v.GetShowAllMail(),
+										"updateCh":    v.GetUpdateChannel(),
+										"autoUpdate":  v.GetAutoUpdate(),
+										"rollout":     v.GetUpdateRollout(),
+										"DoH":         v.GetProxyAllowed(),
+									}).Info("Vault loaded")
+
 									// Load the cookies from the vault.
-								return withCookieJar(vault, func(cookieJar http.CookieJar) error {
+									return withCookieJar(v, func(cookieJar http.CookieJar) error {
 										// Create a new bridge instance.
-									return withBridge(c, exe, locations, version, identifier, crashHandler, reporter, vault, cookieJar, func(b *bridge.Bridge, eventCh <-chan events.Event) error {
+										return withBridge(c, exe, locations, version, identifier, crashHandler, reporter, v, cookieJar, keychains, func(b *bridge.Bridge, eventCh <-chan events.Event) error {
 											if insecure {
 												logrus.Warn("The vault key could not be retrieved; the vault will not be encrypted")
 												b.PushError(bridge.ErrVaultInsecure)
@@ -252,6 +330,9 @@ func run(c *cli.Context) error { //nolint:funlen
 												b.PushError(bridge.ErrVaultCorrupt)
 											}
 
+											// Remove old updates files
+											b.RemoveOldUpdates()
+
 											// Run the frontend.
 											return runFrontend(c, crashHandler, restarter, locations, b, eventCh, quitCh, c.Int(flagParentPID))
 										})
@@ -263,18 +344,26 @@ func run(c *cli.Context) error { //nolint:funlen
 				})
 			})
 		})
+	})
+
+	// if an error occurs, it must be logged now because we're about to close the log file.
+	if err != nil {
+		logrus.Fatal(err)
+	}
+
+	return err
 }
 
 // If there's another instance already running, try to raise it and exit.
-func withSingleInstance(locations *locations.Locations, version *semver.Version, fn func() error) error {
+func withSingleInstance(settingPath, lockFile string, version *semver.Version, fn func() error) error {
 	logrus.Debug("Checking for other instances")
 	defer logrus.Debug("Single instance stopped")
 
-	lock, err := checkSingleInstance(locations.GetLockFile(), version)
+	lock, err := checkSingleInstance(settingPath, lockFile, version)
 	if err != nil {
 		logrus.Info("Another instance is already running; raising it")
 
-		if ok := focus.TryRaise(); !ok {
+		if ok := focus.TryRaise(settingPath); !ok {
 			return fmt.Errorf("another instance is already running but it could not be raised")
 		}
 
@@ -293,7 +382,7 @@ func withSingleInstance(locations *locations.Locations, version *semver.Version,
 }
 
 // Initialize our logging system.
-func withLogging(c *cli.Context, crashHandler *crash.Handler, locations *locations.Locations, fn func() error) error {
+func withLogging(c *cli.Context, crashHandler *crash.Handler, locations *locations.Locations, fn func(closer io.Closer) error) error {
 	logrus.Debug("Initializing logging")
 	defer logrus.Debug("Logging stopped")
 
@@ -306,23 +395,52 @@ func withLogging(c *cli.Context, crashHandler *crash.Handler, locations *locatio
 	logrus.WithField("path", logsPath).Debug("Received logs path")
 
 	// Initialize logging.
-	if err := logging.Init(logsPath, c.String(flagLogLevel)); err != nil {
+	sessionID := logging.NewSessionIDFromString(c.String(FlagSessionID))
+	var closer io.Closer
+	if closer, err = logging.Init(
+		logsPath,
+		sessionID,
+		logging.BridgeShortAppName,
+		logging.DefaultMaxLogFileSize,
+		logging.DefaultPruningSize,
+		c.String(flagLogLevel),
+	); err != nil {
 		return fmt.Errorf("could not initialize logging: %w", err)
 	}
 
 	// Ensure we dump a stack trace if we crash.
-	crashHandler.AddRecoveryAction(logging.DumpStackTrace(logsPath))
+	crashHandler.AddRecoveryAction(logging.DumpStackTrace(logsPath, sessionID, appShortName))
 
 	logrus.
 		WithField("appName", constants.FullAppName).
 		WithField("version", constants.Version).
 		WithField("revision", constants.Revision).
+		WithField("tag", constants.Tag).
 		WithField("build", constants.BuildTime).
 		WithField("runtime", runtime.GOOS).
 		WithField("args", os.Args).
+		WithField("SentryID", sentry.GetProtectedHostname()).
 		Info("Run app")
 
-	return fn()
+	now := time.Now()
+	logrus.
+		WithField("timeZone", now.Format("MST")).
+		WithField("offset", now.Format("-07:00:00")).
+		Info("Time zone info")
+
+	host, err := sysinfo.Host()
+	if err != nil {
+		logrus.WithError(err).Error("Could not retrieve operating system info")
+	} else {
+		osInfo := host.Info().OS
+		logrus.
+			WithField("name", osInfo.Name).
+			WithField("version", osInfo.Version).
+			WithField("build", osInfo.Build).
+			Info("Operating system info")
+	}
+
+	return fn(closer)
 }
 
 // WithLocations provides access to locations where we store our files.
@@ -349,6 +467,11 @@ func withProfiler(c *cli.Context, fn func() error) error {
 		defer profile.Start(profile.CPUProfile, profile.ProfilePath(".")).Stop()
 	}
 
+	if c.Bool(flagTraceProfile) {
+		logrus.Debug("Running with Trace profiling")
+		defer profile.Start(profile.TraceProfile, profile.ProfilePath(".")).Stop()
+	}
+
 	if c.Bool(flagMemProfile) {
 		logrus.Debug("Running with memory profiling")
 		defer profile.Start(profile.MemProfile, profile.MemProfileAllocs, profile.ProfilePath(".")).Stop()
@@ -374,7 +497,7 @@ func withCrashHandler(restarter *restarter.Restarter, reporter *sentry.Reporter,
 	defer logrus.Debug("Crash handler stopped")
 
 	crashHandler := crash.NewHandler(crash.ShowErrorNotification(constants.FullAppName))
-	defer crashHandler.HandlePanic()
+	defer async.HandlePanic(crashHandler)
 
 	// On crash, send crash report to Sentry.
 	crashHandler.AddRecoveryAction(reporter.ReportException)
@@ -411,6 +534,10 @@ func withCookieJar(vault *vault.Vault, fn func(http.CookieJar) error) error {
 		return fmt.Errorf("could not create cookie jar: %w", err)
 	}
 
+	if err := setDeviceCookies(persister); err != nil {
+		return fmt.Errorf("could not set device cookies: %w", err)
+	}
+
 	// Persist the cookies to the vault when we close.
 	defer func() {
 		logrus.Debug("Persisting cookies")
@@ -422,3 +549,33 @@ func withCookieJar(vault *vault.Vault, fn func(http.CookieJar) error) error {
 
 	return fn(persister)
 }
+
+// WithKeychainList init the list of usable keychains.
+func WithKeychainList(panicHandler async.PanicHandler, fn func(*keychain.List) error) error {
+	logrus.Debug("Creating keychain list")
+	defer logrus.Debug("Keychain list stop")
+	defer async.HandlePanic(panicHandler)
+	return fn(keychain.NewList())
+}
+
+func setDeviceCookies(jar *cookies.Jar) error {
+	url, err := url.Parse(constants.APIHost)
+	if err != nil {
+		return err
+	}
+
+	for name, value := range map[string]string{
+		"hhn": sentry.GetProtectedHostname(),
+		"tz":  sentry.GetTimeZone(),
+		"lng": sentry.GetSystemLang(),
+		"clr": string(theme.DefaultTheme()),
+	} {
+		jar.SetCookies(url, []*http.Cookie{{Name: name, Value: value, Secure: true}})
+	}
+
+	return nil
+}
+
+func onMacOS() bool {
+	return runtime.GOOS == "darwin"
+}

internal/app/bridge.go

@@ -1,4 +1,4 @@
-// Copyright (c) 2023 Proton AG
+// Copyright (c) 2025 Proton AG
 //
 // This file is part of Proton Mail Bridge.
 //
@@ -23,6 +23,7 @@ import (
 	"runtime"
 
 	"github.com/Masterminds/semver/v3"
+	"github.com/ProtonMail/gluon/imap"
 	"github.com/ProtonMail/go-autostart"
 	"github.com/ProtonMail/gopenpgp/v2/crypto"
 	"github.com/ProtonMail/proton-bridge/v3/internal/bridge"
@@ -36,17 +37,16 @@ import (
 	"github.com/ProtonMail/proton-bridge/v3/internal/useragent"
 	"github.com/ProtonMail/proton-bridge/v3/internal/vault"
 	"github.com/ProtonMail/proton-bridge/v3/internal/versioner"
+	"github.com/ProtonMail/proton-bridge/v3/pkg/keychain"
 	"github.com/sirupsen/logrus"
 	"github.com/urfave/cli/v2"
 )
 
-const vaultSecretName = "bridge-vault-key"
-
 // deleteOldGoIMAPFiles Set with `-ldflags -X app.deleteOldGoIMAPFiles=true` to enable cleanup of old imap cache data.
 var deleteOldGoIMAPFiles bool //nolint:gochecknoglobals
 
-// withBridge creates creates and tears down the bridge.
-func withBridge( //nolint:funlen
+// withBridge creates and tears down the bridge.
+func withBridge(
 	c *cli.Context,
 	exe string,
 	locations *locations.Locations,
@@ -56,6 +56,7 @@ func withBridge( //nolint:funlen
 	reporter *sentry.Reporter,
 	vault *vault.Vault,
 	cookieJar http.CookieJar,
+	keychains *keychain.List,
 	fn func(*bridge.Bridge, <-chan events.Event) error,
 ) error {
 	logrus.Debug("Creating bridge")
@@ -79,7 +80,7 @@ func withBridge( //nolint:funlen
 	)
 
 	// Create a proxy dialer which switches to a proxy if the request fails.
-	proxyDialer := dialer.NewProxyTLSDialer(pinningDialer, constants.APIHost)
+	proxyDialer := dialer.NewProxyTLSDialer(pinningDialer, constants.APIHost, crashHandler)
 
 	// Create the autostarter.
 	autostarter := newAutostarter(exe)
@@ -98,6 +99,7 @@ func withBridge( //nolint:funlen
 		autostarter,
 		updater,
 		version,
+		keychains,
 
 		// The API stuff.
 		constants.APIHost,
@@ -110,6 +112,8 @@ func withBridge( //nolint:funlen
 		// Crash and report stuff
 		crashHandler,
 		reporter,
+		imap.DefaultEpochUIDValidityGenerator(),
+		nil,
 
 		// The logging stuff.
 		c.String(flagLogIMAP) == "client" || c.String(flagLogIMAP) == "all",
@@ -155,7 +159,7 @@ func newUpdater(locations *locations.Locations) (*updater.Updater, error) {
 	}
 
 	return updater.NewUpdater(
-		updater.NewInstaller(versioner.New(updatesDir)),
+		versioner.New(updatesDir),
 		verifier,
 		constants.UpdateName,
 		runtime.GOOS,

internal/app/frontend.go

@@ -1,4 +1,4 @@
-// Copyright (c) 2023 Proton AG
+// Copyright (c) 2025 Proton AG
 //
 // This file is part of Proton Mail Bridge.
 //
@@ -46,10 +46,11 @@ func runFrontend(
 
 	switch {
 	case c.Bool(flagCLI):
-		return bridgeCLI.New(bridge, restarter, eventCh).Loop()
+		return bridgeCLI.New(bridge, restarter, eventCh, crashHandler, quitCh).Loop()
 
 	case c.Bool(flagNonInteractive):
-		select {}
+		<-quitCh
+		return nil
 
 	case c.Bool(flagGRPC):
 		service, err := grpc.NewService(crashHandler, restarter, locations, bridge, eventCh, quitCh, !c.Bool(flagNoWindow), parentPID)

internal/app/migration.go

@@ -1,4 +1,4 @@
-// Copyright (c) 2023 Proton AG
+// Copyright (c) 2025 Proton AG
 //
 // This file is part of Proton Mail Bridge.
 //
@@ -43,7 +43,7 @@ import (
 
 // nolint:gosec
 func migrateKeychainHelper(locations *locations.Locations) error {
-	logrus.Info("Migrating keychain helper")
+	logrus.Trace("Checking if keychain helper needs to be migrated")
 
 	settings, err := locations.ProvideSettingsPath()
 	if err != nil {
@@ -75,7 +75,11 @@ func migrateKeychainHelper(locations *locations.Locations) error {
 		return fmt.Errorf("failed to unmarshal old prefs file: %w", err)
 	}
 
-	return vault.SetHelper(settings, prefs.Helper)
+	err = vault.SetHelper(settings, prefs.Helper)
+	if err == nil {
+		logrus.Info("Keychain helper has been migrated")
+	}
+	return err
 }
 
 // nolint:gosec
@@ -87,6 +91,11 @@ func migrateOldSettings(v *vault.Vault) error {
 		return fmt.Errorf("failed to get user config dir: %w", err)
 	}
 
+	return migrateOldSettingsWithDir(configDir, v)
+}
+
+// nolint:gosec
+func migrateOldSettingsWithDir(configDir string, v *vault.Vault) error {
 	b, err := os.ReadFile(filepath.Join(configDir, "protonmail", "bridge", "prefs.json"))
 	if errors.Is(err, fs.ErrNotExist) {
 		return nil
@@ -94,10 +103,30 @@ func migrateOldSettings(v *vault.Vault) error {
 		return fmt.Errorf("failed to read old prefs file: %w", err)
 	}
 
-	return migratePrefsToVault(v, b)
+	if err := migratePrefsToVault(v, b); err != nil {
+		return fmt.Errorf("failed to migrate prefs to vault: %w", err)
+	}
+
+	logrus.Info("Migrating TLS certificate")
+
+	certPEM, err := os.ReadFile(filepath.Join(configDir, "protonmail", "bridge", "cert.pem"))
+	if errors.Is(err, fs.ErrNotExist) {
+		return nil
+	} else if err != nil {
+		return fmt.Errorf("failed to read old cert file: %w", err)
+	}
+
+	keyPEM, err := os.ReadFile(filepath.Join(configDir, "protonmail", "bridge", "key.pem"))
+	if errors.Is(err, fs.ErrNotExist) {
+		return nil
+	} else if err != nil {
+		return fmt.Errorf("failed to read old key file: %w", err)
+	}
+
+	return v.SetBridgeTLSCertKey(certPEM, keyPEM)
 }
 
-func migrateOldAccounts(locations *locations.Locations, v *vault.Vault) error {
+func migrateOldAccounts(locations *locations.Locations, keychains *keychain.List, v *vault.Vault) error {
 	logrus.Info("Migrating accounts")
 
 	settings, err := locations.ProvideSettingsPath()
@@ -109,8 +138,7 @@ func migrateOldAccounts(locations *locations.Locations, v *vault.Vault) error {
 	if err != nil {
 		return fmt.Errorf("failed to get helper: %w", err)
 	}
-
-	keychain, err := keychain.NewKeychain(helper, "bridge")
+	keychain, err := keychain.NewKeychain(helper, "bridge", keychains.GetHelpers(), keychains.GetDefaultHelper())
 	if err != nil {
 		return fmt.Errorf("failed to create keychain: %w", err)
 	}
@@ -187,7 +215,6 @@ func migrateOldAccount(userID string, store *credentials.Store, v *vault.Vault)
 	return nil
 }
 
-// nolint:funlen
 func migratePrefsToVault(vault *vault.Vault, b []byte) error {
 	var prefs struct {
 		IMAPPort int  `json:"user_port_imap,,string"`
@@ -265,14 +292,6 @@ func migratePrefsToVault(vault *vault.Vault, b []byte) error {
 		errs = multierror.Append(errs, fmt.Errorf("failed to migrate show all mail: %w", err))
 	}
 
-	if err := vault.SetSyncWorkers(prefs.FetchWorkers); err != nil {
-		errs = multierror.Append(errs, fmt.Errorf("failed to migrate sync workers: %w", err))
-	}
-
-	if err := vault.SetSyncAttPool(prefs.AttachmentWorkers); err != nil {
-		errs = multierror.Append(errs, fmt.Errorf("failed to migrate sync attachment pool: %w", err))
-	}
-
 	if err := vault.SetCookies([]byte(prefs.Cookies)); err != nil {
 		errs = multierror.Append(errs, fmt.Errorf("failed to migrate cookies: %w", err))
 	}

internal/app/migration_test.go

@@ -1,4 +1,4 @@
-// Copyright (c) 2023 Proton AG
+// Copyright (c) 2025 Proton AG
 //
 // This file is part of Proton Mail Bridge.
 //
@@ -25,6 +25,7 @@ import (
 	"runtime"
 	"testing"
 
+	"github.com/ProtonMail/gluon/async"
 	"github.com/ProtonMail/gopenpgp/v2/crypto"
 	"github.com/ProtonMail/proton-bridge/v3/internal/bridge"
 	"github.com/ProtonMail/proton-bridge/v3/internal/cookies"
@@ -34,57 +35,52 @@ import (
 	"github.com/ProtonMail/proton-bridge/v3/internal/vault"
 	"github.com/ProtonMail/proton-bridge/v3/pkg/algo"
 	"github.com/ProtonMail/proton-bridge/v3/pkg/keychain"
-	dockerCredentials "github.com/docker/docker-credential-helpers/credentials"
 	"github.com/stretchr/testify/require"
 )
 
-func TestMigratePrefsToVault(t *testing.T) {
+func TestMigratePrefsToVaultWithKeys(t *testing.T) {
 	// Create a new vault.
-	vault, corrupt, err := vault.New(t.TempDir(), t.TempDir(), []byte("my secret key"))
+	vault, corrupt, err := vault.New(t.TempDir(), t.TempDir(), []byte("my secret key"), async.NoopPanicHandler{})
 	require.NoError(t, err)
-	require.False(t, corrupt)
+	require.NoError(t, corrupt)
 
 	// load the old prefs file.
-	b, err := os.ReadFile(filepath.Join("testdata", "prefs.json"))
-	require.NoError(t, err)
+	configDir := filepath.Join("testdata", "with_keys")
 
 	// Migrate the old prefs file to the new vault.
-	require.NoError(t, migratePrefsToVault(vault, b))
+	require.NoError(t, migrateOldSettingsWithDir(configDir, vault))
 
-	// Check that the IMAP and SMTP prefs are migrated.
-	require.Equal(t, 2143, vault.GetIMAPPort())
-	require.Equal(t, 2025, vault.GetSMTPPort())
-	require.True(t, vault.GetSMTPSSL())
+	// Check Json Settings
+	validateJSONPrefs(t, vault)
 
-	// Check that the update channel is migrated.
-	require.True(t, vault.GetAutoUpdate())
-	require.Equal(t, updater.EarlyChannel, vault.GetUpdateChannel())
-	require.Equal(t, 0.4849529004202015, vault.GetUpdateRollout())
+	cert, key := vault.GetBridgeTLSCert()
+	// Check the keys were found and collected.
+	require.Equal(t, "-----BEGIN CERTIFICATE-----", string(cert))
+	require.Equal(t, "-----BEGIN RSA PRIVATE KEY-----", string(key))
+}
 
-	// Check that the app settings have been migrated.
-	require.False(t, vault.GetFirstStart())
-	require.Equal(t, "blablabla", vault.GetColorScheme())
-	require.Equal(t, "2.3.0+git", vault.GetLastVersion().String())
-	require.True(t, vault.GetAutostart())
-
-	// Check that the other app settings have been migrated.
-	require.Equal(t, 16, vault.SyncWorkers())
-	require.Equal(t, 16, vault.SyncAttPool())
-	require.False(t, vault.GetProxyAllowed())
-	require.False(t, vault.GetShowAllMail())
-
-	// Check that the cookies have been migrated.
-	jar, err := cookiejar.New(nil)
+func TestMigratePrefsToVaultWithoutKeys(t *testing.T) {
+	// Create a new vault.
+	vault, corrupt, err := vault.New(t.TempDir(), t.TempDir(), []byte("my secret key"), async.NoopPanicHandler{})
 	require.NoError(t, err)
+	require.NoError(t, corrupt)
 
-	cookies, err := cookies.NewCookieJar(jar, vault)
-	require.NoError(t, err)
+	// load the old prefs file.
+	configDir := filepath.Join("testdata", "without_keys")
 
-	url, err := url.Parse("https://api.protonmail.ch")
-	require.NoError(t, err)
+	// Migrate the old prefs file to the new vault.
+	require.NoError(t, migrateOldSettingsWithDir(configDir, vault))
 
-	// There should be a cookie for the API.
-	require.NotEmpty(t, cookies.Cookies(url))
+	// Migrate the old prefs file to the new vault.
+	require.NoError(t, migrateOldSettingsWithDir(configDir, vault))
+
+	// Check Json Settings
+	validateJSONPrefs(t, vault)
+
+	// Check the keys were found and collected.
+	cert, key := vault.GetBridgeTLSCert()
+	require.NotEqual(t, []byte("-----BEGIN CERTIFICATE-----"), cert)
+	require.NotEqual(t, []byte("-----BEGIN RSA PRIVATE KEY-----"), key)
 }
 
 func TestKeychainMigration(t *testing.T) {
@@ -101,7 +97,7 @@ func TestKeychainMigration(t *testing.T) {
 		oldCacheDir := filepath.Join(tmpDir, "protonmail", "bridge")
 		require.NoError(t, os.MkdirAll(oldCacheDir, 0o700))
 
-		oldPrefs, err := os.ReadFile(filepath.Join("testdata", "prefs.json"))
+		oldPrefs, err := os.ReadFile(filepath.Join("testdata", "without_keys", "protonmail", "bridge", "prefs.json"))
 		require.NoError(t, err)
 
 		require.NoError(t, os.WriteFile(
@@ -136,11 +132,9 @@ func TestKeychainMigration(t *testing.T) {
 }
 
 func TestUserMigration(t *testing.T) {
-	keychainHelper := keychain.NewTestHelper()
+	kcl := keychain.NewTestKeychainsList()
 
-	keychain.Helpers["mock"] = func(string) (dockerCredentials.Helper, error) { return keychainHelper, nil }
-
-	kc, err := keychain.NewKeychain("mock", "bridge")
+	kc, err := keychain.NewKeychain("mock", "bridge", kcl.GetHelpers(), kcl.GetDefaultHelper())
 	require.NoError(t, err)
 
 	require.NoError(t, kc.Put("brokenID", "broken"))
@@ -177,11 +171,11 @@ func TestUserMigration(t *testing.T) {
 	token, err := crypto.RandomToken(32)
 	require.NoError(t, err)
 
-	v, corrupt, err := vault.New(settingsFolder, settingsFolder, token)
+	v, corrupt, err := vault.New(settingsFolder, settingsFolder, token, async.NoopPanicHandler{})
 	require.NoError(t, err)
-	require.False(t, corrupt)
+	require.NoError(t, corrupt)
 
-	require.NoError(t, migrateOldAccounts(locations, v))
+	require.NoError(t, migrateOldAccounts(locations, kcl, v))
 	require.Equal(t, []string{wantCredentials.UserID}, v.GetUserIDs())
 
 	require.NoError(t, v.GetUser(wantCredentials.UserID, func(u *vault.User) {
@@ -196,3 +190,38 @@ func TestUserMigration(t *testing.T) {
 		require.Equal(t, vault.CombinedMode, u.AddressMode())
 	}))
 }
+
+func validateJSONPrefs(t *testing.T, vault *vault.Vault) {
+	// Check that the IMAP and SMTP prefs are migrated.
+	require.Equal(t, 2143, vault.GetIMAPPort())
+	require.Equal(t, 2025, vault.GetSMTPPort())
+	require.True(t, vault.GetSMTPSSL())
+
+	// Check that the update channel is migrated.
+	require.True(t, vault.GetAutoUpdate())
+	require.Equal(t, updater.EarlyChannel, vault.GetUpdateChannel())
+	require.Equal(t, 0.4849529004202015, vault.GetUpdateRollout())
+
+	// Check that the app settings have been migrated.
+	require.False(t, vault.GetFirstStart())
+	require.Equal(t, "blablabla", vault.GetColorScheme())
+	require.Equal(t, "2.3.0+git", vault.GetLastVersion().String())
+	require.True(t, vault.GetAutostart())
+
+	// Check that the other app settings have been migrated.
+	require.False(t, vault.GetProxyAllowed())
+	require.False(t, vault.GetShowAllMail())
+
+	// Check that the cookies have been migrated.
+	jar, err := cookiejar.New(nil)
+	require.NoError(t, err)
+
+	cookies, err := cookies.NewCookieJar(jar, vault)
+	require.NoError(t, err)
+
+	url, err := url.Parse("https://api.protonmail.ch")
+	require.NoError(t, err)
+
+	// There should be a cookie for the API.
+	require.NotEmpty(t, cookies.Cookies(url))
+}

internal/app/singleinstance.go

@@ -1,4 +1,4 @@
-// Copyright (c) 2023 Proton AG
+// Copyright (c) 2025 Proton AG
 //
 // This file is part of Proton Mail Bridge.
 //
@@ -34,17 +34,17 @@ import (
 //
 // For macOS and Linux when already running version is older than this instance
 // it will kill old and continue with this new bridge (i.e. no error returned).
-func checkSingleInstance(lockFilePath string, curVersion *semver.Version) (*os.File, error) {
+func checkSingleInstance(settingPath, lockFilePath string, curVersion *semver.Version) (*os.File, error) {
 	if lock, err := singleinstance.CreateLockFile(lockFilePath); err == nil {
 		logrus.WithField("path", lockFilePath).Debug("Created lock file; no other instance is running")
 		return lock, nil
 	}
 
-	logrus.Debug("Failed to create lock file; another instance is running")
+	logrus.Warn("Failed to create lock file; another instance is running")
 
 	// We couldn't create the lock file, so another instance is probably running.
 	// Check if it's an older version of the app.
-	lastVersion, ok := focus.TryVersion()
+	lastVersion, ok := focus.TryVersion(settingPath)
 	if !ok {
 		return nil, fmt.Errorf("failed to determine version of running instance")
 	}

internal/app/testdata/with_keys/protonmail/bridge/cert.pem

@@ -0,0 +1 @@
+-----BEGIN CERTIFICATE-----

internal/app/testdata/with_keys/protonmail/bridge/key.pem

@@ -0,0 +1 @@
+-----BEGIN RSA PRIVATE KEY-----

internal/app/testdata/without_keys/protonmail/bridge/prefs.json

@@ -0,0 +1,31 @@
+{
+	"allow_proxy": "false",
+	"attachment_workers": "16",
+	"autostart": "true",
+	"autoupdate": "true",
+	"cache_compression": "true",
+	"cache_concurrent_read": "16",
+	"cache_concurrent_write": "16",
+	"cache_enabled": "true",
+	"cache_location": "/home/user/.config/protonmail/bridge/cache/c11/messages",
+	"cache_min_free_abs": "250000000",
+	"cache_min_free_rat": "",
+	"color_scheme": "blablabla",
+	"cookies": "{\"https://api.protonmail.ch\":[{\"Name\":\"Session-Id\",\"Value\":\"blablablablablablablablabla\",\"Path\":\"/\",\"Domain\":\"protonmail.ch\",\"Expires\":\"2023-02-19T00:20:40.269424437+01:00\",\"RawExpires\":\"\",\"MaxAge\":7776000,\"Secure\":true,\"HttpOnly\":true,\"SameSite\":0,\"Raw\":\"Session-Id=blablablablablablablablabla; Domain=protonmail.ch; Path=/; HttpOnly; Secure; Max-Age=7776000\",\"Unparsed\":null},{\"Name\":\"Tag\",\"Value\":\"default\",\"Path\":\"/\",\"Domain\":\"\",\"Expires\":\"2023-02-19T00:20:40.269428627+01:00\",\"RawExpires\":\"\",\"MaxAge\":7776000,\"Secure\":true,\"HttpOnly\":false,\"SameSite\":0,\"Raw\":\"Tag=default; Path=/; Secure; Max-Age=7776000\",\"Unparsed\":null}],\"https://protonmail.com\":[{\"Name\":\"Session-Id\",\"Value\":\"blablablablablablablablabla\",\"Path\":\"/\",\"Domain\":\"protonmail.com\",\"Expires\":\"2023-02-19T00:20:18.315084712+01:00\",\"RawExpires\":\"\",\"MaxAge\":7776000,\"Secure\":true,\"HttpOnly\":true,\"SameSite\":0,\"Raw\":\"Session-Id=Y3q2Mh-ClvqL6LWeYdfyPgAAABI; Domain=protonmail.com; Path=/; HttpOnly; Secure; Max-Age=7776000\",\"Unparsed\":null},{\"Name\":\"Tag\",\"Value\":\"redirect\",\"Path\":\"/\",\"Domain\":\"\",\"Expires\":\"2023-02-19T00:20:18.315087646+01:00\",\"RawExpires\":\"\",\"MaxAge\":7776000,\"Secure\":true,\"HttpOnly\":false,\"SameSite\":0,\"Raw\":\"Tag=redirect; Path=/; Secure; Max-Age=7776000\",\"Unparsed\":null}]}",
+	"fetch_workers": "16",
+	"first_time_start": "false",
+	"first_time_start_gui": "true",
+	"imap_workers": "16",
+	"is_all_mail_visible": "false",
+	"last_heartbeat": "325",
+	"last_used_version": "2.3.0+git",
+	"preferred_keychain": "secret-service",
+	"rebranding_migrated": "true",
+	"report_outgoing_email_without_encryption": "false",
+	"rollout": "0.4849529004202015",
+	"user_port_api": "1042",
+	"update_channel": "early",
+	"user_port_imap": "2143",
+	"user_port_smtp": "2025",
+	"user_ssl_smtp": "true"
+}

internal/app/vault.go

@@ -1,4 +1,4 @@
-// Copyright (c) 2023 Proton AG
+// Copyright (c) 2025 Proton AG
 //
 // This file is part of Proton Mail Bridge.
 //
@@ -18,59 +18,50 @@
 package app
 
 import (
-	"encoding/base64"
 	"fmt"
 	"path"
 
-	"github.com/ProtonMail/gopenpgp/v2/crypto"
+	"github.com/ProtonMail/gluon/async"
 	"github.com/ProtonMail/proton-bridge/v3/internal/certs"
 	"github.com/ProtonMail/proton-bridge/v3/internal/constants"
 	"github.com/ProtonMail/proton-bridge/v3/internal/locations"
+	"github.com/ProtonMail/proton-bridge/v3/internal/sentry"
 	"github.com/ProtonMail/proton-bridge/v3/internal/vault"
 	"github.com/ProtonMail/proton-bridge/v3/pkg/keychain"
 	"github.com/sirupsen/logrus"
-	"golang.org/x/exp/slices"
 )
 
-func WithVault(locations *locations.Locations, fn func(*vault.Vault, bool, bool) error) error {
+func WithVault(reporter *sentry.Reporter, locations *locations.Locations, keychains *keychain.List, panicHandler async.PanicHandler, fn func(*vault.Vault, bool, bool) error) error {
 	logrus.Debug("Creating vault")
 	defer logrus.Debug("Vault stopped")
 
 	// Create the encVault.
-	encVault, insecure, corrupt, err := newVault(locations)
+	encVault, insecure, corrupt, err := newVault(reporter, locations, keychains, panicHandler)
 	if err != nil {
 		return fmt.Errorf("could not create vault: %w", err)
 	}
 
 	logrus.WithFields(logrus.Fields{
 		"insecure": insecure,
-		"corrupt":  corrupt,
+		"corrupt":  corrupt != nil,
 	}).Debug("Vault created")
 
-	// Install the certificates if needed.
-	if installed := encVault.GetCertsInstalled(); !installed {
-		logrus.Debug("Installing certificates")
-
-		if err := certs.NewInstaller().InstallCert(encVault.GetBridgeTLSCert()); err != nil {
-			return fmt.Errorf("failed to install certs: %w", err)
+	if corrupt != nil {
+		logrus.WithError(corrupt).Warn("Failed to load existing vault, vault has been reset")
 	}
 
-		if err := encVault.SetCertsInstalled(true); err != nil {
-			return fmt.Errorf("failed to set certs installed: %w", err)
-		}
-
-		logrus.Debug("Certificates successfully installed")
-	}
+	cert, _ := encVault.GetBridgeTLSCert()
+	certs.NewInstaller().LogCertInstallStatus(cert)
 
 	// GODT-1950: Add teardown actions (e.g. to close the vault).
 
-	return fn(encVault, insecure, corrupt)
+	return fn(encVault, insecure, corrupt != nil)
 }
 
-func newVault(locations *locations.Locations) (*vault.Vault, bool, bool, error) {
+func newVault(reporter *sentry.Reporter, locations *locations.Locations, keychains *keychain.List, panicHandler async.PanicHandler) (*vault.Vault, bool, error, error) {
 	vaultDir, err := locations.ProvideSettingsPath()
 	if err != nil {
-		return nil, false, false, fmt.Errorf("could not get vault dir: %w", err)
+		return nil, false, nil, fmt.Errorf("could not get vault dir: %w", err)
 	}
 
 	logrus.WithField("vaultDir", vaultDir).Debug("Loading vault from directory")
@@ -80,7 +71,18 @@ func newVault(locations *locations.Locations) (*vault.Vault, bool, bool, error)
 		insecure bool
 	)
 
-	if key, err := getVaultKey(vaultDir); err != nil {
+	if key, err := loadVaultKey(vaultDir, keychains); err != nil {
+		if reporter != nil {
+			if rerr := reporter.ReportMessageWithContext("Could not load/create vault key", map[string]any{
+				"keychainDefaultHelper":       keychains.GetDefaultHelper(),
+				"keychainUsableHelpersLength": len(keychains.GetHelpers()),
+				"error":                       err.Error(),
+			}); rerr != nil {
+				logrus.WithError(err).Info("Failed to report keychain issue to Sentry")
+			}
+		}
+
+		logrus.WithError(err).Error("Could not load/create vault key")
 		insecure = true
 
 		// We store the insecure vault in a separate directory
@@ -91,53 +93,37 @@ func newVault(locations *locations.Locations) (*vault.Vault, bool, bool, error)
 
 	gluonCacheDir, err := locations.ProvideGluonCachePath()
 	if err != nil {
-		return nil, false, false, fmt.Errorf("could not provide gluon path: %w", err)
+		return nil, false, nil, fmt.Errorf("could not provide gluon path: %w", err)
 	}
 
-	vault, corrupt, err := vault.New(vaultDir, gluonCacheDir, vaultKey)
+	vault, corrupt, err := vault.New(vaultDir, gluonCacheDir, vaultKey, panicHandler)
 	if err != nil {
-		return nil, false, false, fmt.Errorf("could not create vault: %w", err)
+		return nil, false, corrupt, fmt.Errorf("could not create vault: %w", err)
 	}
 
 	return vault, insecure, corrupt, nil
 }
 
-func getVaultKey(vaultDir string) ([]byte, error) {
+func loadVaultKey(vaultDir string, keychains *keychain.List) ([]byte, error) {
 	helper, err := vault.GetHelper(vaultDir)
 	if err != nil {
 		return nil, fmt.Errorf("could not get keychain helper: %w", err)
 	}
 
-	keychain, err := keychain.NewKeychain(helper, constants.KeyChainName)
+	kc, err := keychain.NewKeychain(helper, constants.KeyChainName, keychains.GetHelpers(), keychains.GetDefaultHelper())
 	if err != nil {
 		return nil, fmt.Errorf("could not create keychain: %w", err)
 	}
 
-	secrets, err := keychain.List()
+	key, err := vault.GetVaultKey(kc)
 	if err != nil {
-		return nil, fmt.Errorf("could not list keychain: %w", err)
+		if keychain.IsErrKeychainNoItem(err) {
+			logrus.WithError(err).Warn("no vault key found, generating new")
+			return vault.NewVaultKey(kc)
 		}
 
-	if !slices.Contains(secrets, vaultSecretName) {
-		tok, err := crypto.RandomToken(32)
-		if err != nil {
-			return nil, fmt.Errorf("could not generate random token: %w", err)
+		return nil, fmt.Errorf("could not check for vault key: %w", err)
 	}
 
-		if err := keychain.Put(vaultSecretName, base64.StdEncoding.EncodeToString(tok)); err != nil {
-			return nil, fmt.Errorf("could not put keychain item: %w", err)
-		}
-	}
-
-	_, keyEnc, err := keychain.Get(vaultSecretName)
-	if err != nil {
-		return nil, fmt.Errorf("could not get keychain item: %w", err)
-	}
-
-	keyDec, err := base64.StdEncoding.DecodeString(keyEnc)
-	if err != nil {
-		return nil, fmt.Errorf("could not decode keychain item: %w", err)
-	}
-
-	return keyDec, nil
+	return key, nil
 }

internal/async/context.go

@@ -1,82 +0,0 @@
-// Copyright (c) 2023 Proton AG
-//
-// This file is part of Proton Mail Bridge.
-//
-// Proton Mail Bridge is free software: you can redistribute it and/or modify
-// it under the terms of the GNU General Public License as published by
-// the Free Software Foundation, either version 3 of the License, or
-// (at your option) any later version.
-//
-// Proton Mail Bridge is distributed in the hope that it will be useful,
-// but WITHOUT ANY WARRANTY; without even the implied warranty of
-// MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
-// GNU General Public License for more details.
-//
-// You should have received a copy of the GNU General Public License
-// along with Proton Mail Bridge.  If not, see <https://www.gnu.org/licenses/>.
-
-package async
-
-import (
-	"context"
-	"sync"
-)
-
-// Abortable collects groups of functions that can be aborted by calling Abort.
-type Abortable struct {
-	abortFunc []context.CancelFunc
-	abortLock sync.RWMutex
-}
-
-func (a *Abortable) Do(ctx context.Context, fn func(context.Context)) {
-	fn(a.newCancelCtx(ctx))
-}
-
-func (a *Abortable) Abort() {
-	a.abortLock.RLock()
-	defer a.abortLock.RUnlock()
-
-	for _, fn := range a.abortFunc {
-		fn()
-	}
-}
-
-func (a *Abortable) newCancelCtx(ctx context.Context) context.Context {
-	a.abortLock.Lock()
-	defer a.abortLock.Unlock()
-
-	ctx, cancel := context.WithCancel(ctx)
-
-	a.abortFunc = append(a.abortFunc, cancel)
-
-	return ctx
-}
-
-// RangeContext iterates over the given channel until the context is canceled or the
-// channel is closed.
-func RangeContext[T any](ctx context.Context, ch <-chan T, fn func(T)) {
-	for {
-		select {
-		case v, ok := <-ch:
-			if !ok {
-				return
-			}
-
-			fn(v)
-
-		case <-ctx.Done():
-			return
-		}
-	}
-}
-
-// ForwardContext forwards all values from the src channel to the dst channel until the
-// context is canceled or the src channel is closed.
-func ForwardContext[T any](ctx context.Context, dst chan<- T, src <-chan T) {
-	RangeContext(ctx, src, func(v T) {
-		select {
-		case dst <- v:
-		case <-ctx.Done():
-		}
-	})
-}

internal/async/group.go

@@ -1,233 +0,0 @@
-// Copyright (c) 2023 Proton AG
-//
-// This file is part of Proton Mail Bridge.
-//
-// Proton Mail Bridge is free software: you can redistribute it and/or modify
-// it under the terms of the GNU General Public License as published by
-// the Free Software Foundation, either version 3 of the License, or
-// (at your option) any later version.
-//
-// Proton Mail Bridge is distributed in the hope that it will be useful,
-// but WITHOUT ANY WARRANTY; without even the implied warranty of
-// MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
-// GNU General Public License for more details.
-//
-// You should have received a copy of the GNU General Public License
-// along with Proton Mail Bridge.  If not, see <https://www.gnu.org/licenses/>.
-
-package async
-
-import (
-	"context"
-	"math/rand"
-	"sync"
-	"time"
-)
-
-type PanicHandler interface {
-	HandlePanic()
-}
-
-// Group is forked and improved version of "github.com/bradenaw/juniper/xsync.Group".
-//
-// It manages a group of goroutines. The main change to original is posibility
-// to wait passed function to finish without canceling it's context and adding
-// PanicHandler.
-type Group struct {
-	baseCtx context.Context
-	ctx     context.Context
-	jobCtx  context.Context
-	cancel  context.CancelFunc
-	finish  context.CancelFunc
-	wg      sync.WaitGroup
-
-	panicHandler PanicHandler
-}
-
-// NewGroup returns a Group ready for use. The context passed to any of the f functions will be a
-// descendant of ctx.
-func NewGroup(ctx context.Context, panicHandler PanicHandler) *Group {
-	bgCtx, cancel := context.WithCancel(ctx)
-	jobCtx, finish := context.WithCancel(ctx)
-	return &Group{
-		baseCtx:      ctx,
-		ctx:          bgCtx,
-		jobCtx:       jobCtx,
-		cancel:       cancel,
-		finish:       finish,
-		panicHandler: panicHandler,
-	}
-}
-
-// Once calls f once from another goroutine.
-func (g *Group) Once(f func(ctx context.Context)) {
-	g.wg.Add(1)
-	go func() {
-		defer g.handlePanic()
-
-		f(g.ctx)
-		g.wg.Done()
-	}()
-}
-
-// jitterDuration returns a random duration in [d - jitter, d + jitter].
-func jitterDuration(d time.Duration, jitter time.Duration) time.Duration {
-	return d + time.Duration(float64(jitter)*((rand.Float64()*2)-1)) //nolint:gosec
-}
-
-// Periodic spawns a goroutine that calls f once per interval +/- jitter.
-func (g *Group) Periodic(
-	interval time.Duration,
-	jitter time.Duration,
-	f func(ctx context.Context),
-) {
-	g.wg.Add(1)
-	go func() {
-		defer g.handlePanic()
-
-		defer g.wg.Done()
-
-		t := time.NewTimer(jitterDuration(interval, jitter))
-		defer t.Stop()
-
-		for {
-			if g.ctx.Err() != nil {
-				return
-			}
-
-			select {
-			case <-g.jobCtx.Done():
-				return
-			case <-t.C:
-			}
-
-			t.Reset(jitterDuration(interval, jitter))
-			f(g.ctx)
-		}
-	}()
-}
-
-// Trigger spawns a goroutine which calls f whenever the returned function is called. If f is
-// already running when triggered, f will run again immediately when it finishes.
-func (g *Group) Trigger(f func(ctx context.Context)) func() {
-	c := make(chan struct{}, 1)
-	g.wg.Add(1)
-	go func() {
-		defer g.handlePanic()
-
-		defer g.wg.Done()
-
-		for {
-			if g.ctx.Err() != nil {
-				return
-			}
-			select {
-			case <-g.jobCtx.Done():
-				return
-			case <-c:
-			}
-			f(g.ctx)
-		}
-	}()
-
-	return func() {
-		select {
-		case c <- struct{}{}:
-		default:
-		}
-	}
-}
-
-// PeriodicOrTrigger spawns a goroutine which calls f whenever the returned function is called.  If
-// f is already running when triggered, f will run again immediately when it finishes. Also calls f
-// when it has been interval+/-jitter since the last trigger.
-func (g *Group) PeriodicOrTrigger(
-	interval time.Duration,
-	jitter time.Duration,
-	f func(ctx context.Context),
-) func() {
-	c := make(chan struct{}, 1)
-	g.wg.Add(1)
-	go func() {
-		defer g.handlePanic()
-
-		defer g.wg.Done()
-
-		t := time.NewTimer(jitterDuration(interval, jitter))
-		defer t.Stop()
-
-		for {
-			if g.ctx.Err() != nil {
-				return
-			}
-			select {
-			case <-g.jobCtx.Done():
-				return
-			case <-t.C:
-				t.Reset(jitterDuration(interval, jitter))
-			case <-c:
-				if !t.Stop() {
-					<-t.C
-				}
-				t.Reset(jitterDuration(interval, jitter))
-			}
-			f(g.ctx)
-		}
-	}()
-
-	return func() {
-		select {
-		case c <- struct{}{}:
-		default:
-		}
-	}
-}
-
-func (g *Group) resetCtx() {
-	g.jobCtx, g.finish = context.WithCancel(g.baseCtx)
-	g.ctx, g.cancel = context.WithCancel(g.baseCtx)
-}
-
-// Cancel is send to all of the spawn goroutines and ends periodic
-// or trigger routines.
-func (g *Group) Cancel() {
-	g.cancel()
-	g.finish()
-	g.resetCtx()
-}
-
-// Finish will ends all periodic or polls routines. It will let
-// currently running functions to finish (cancel is not sent).
-//
-// It is not safe to call Wait concurrently with any other method on g.
-func (g *Group) Finish() {
-	g.finish()
-	g.jobCtx, g.finish = context.WithCancel(g.baseCtx)
-}
-
-// CancelAndWait cancels the context passed to any of the spawned goroutines and waits for all spawned
-// goroutines to exit.
-//
-// It is not safe to call Wait concurrently with any other method on g.
-func (g *Group) CancelAndWait() {
-	g.finish()
-	g.cancel()
-	g.wg.Wait()
-	g.resetCtx()
-}
-
-// WaitToFinish will ends all periodic or polls routines. It will wait for
-// currently running functions to finish (cancel is not sent).
-//
-// It is not safe to call Wait concurrently with any other method on g.
-func (g *Group) WaitToFinish() {
-	g.finish()
-	g.wg.Wait()
-	g.jobCtx, g.finish = context.WithCancel(g.baseCtx)
-}
-
-func (g *Group) handlePanic() {
-	if g.panicHandler != nil {
-		g.panicHandler.HandlePanic()
-	}
-}

internal/bridge/api.go

@@ -1,4 +1,4 @@
-// Copyright (c) 2023 Proton AG
+// Copyright (c) 2025 Proton AG
 //
 // This file is part of Proton Mail Bridge.
 //
@@ -21,6 +21,7 @@ import (
 	"net/http"
 
 	"github.com/Masterminds/semver/v3"
+	"github.com/ProtonMail/gluon/async"
 	"github.com/ProtonMail/go-proton-api"
 	"github.com/ProtonMail/proton-bridge/v3/internal/constants"
 	"github.com/sirupsen/logrus"
@@ -32,14 +33,14 @@ func defaultAPIOptions(
 	version *semver.Version,
 	cookieJar http.CookieJar,
 	transport http.RoundTripper,
-	poolSize int,
+	panicHandler async.PanicHandler,
 ) []proton.Option {
 	return []proton.Option{
 		proton.WithHostURL(apiURL),
 		proton.WithAppVersion(constants.AppVersion(version.Original())),
 		proton.WithCookieJar(cookieJar),
 		proton.WithTransport(transport),
-		proton.WithAttPoolSize(poolSize),
-		proton.WithLogger(logrus.StandardLogger()),
+		proton.WithLogger(logrus.WithField("pkg", "gpa/client")),
+		proton.WithPanicHandler(panicHandler),
 	}
 }

internal/bridge/api_default.go

@@ -1,4 +1,4 @@
-// Copyright (c) 2023 Proton AG
+// Copyright (c) 2025 Proton AG
 //
 // This file is part of Proton Mail Bridge.
 //
@@ -15,7 +15,7 @@
 // You should have received a copy of the GNU General Public License
 // along with Proton Mail Bridge.  If not, see <https://www.gnu.org/licenses/>.
 
-//go:build !build_qa
+//go:build !build_qa && !test_integration
 
 package bridge
 
@@ -23,6 +23,7 @@ import (
 	"net/http"
 
 	"github.com/Masterminds/semver/v3"
+	"github.com/ProtonMail/gluon/async"
 	"github.com/ProtonMail/go-proton-api"
 )
 
@@ -32,7 +33,7 @@ func newAPIOptions(
 	version *semver.Version,
 	cookieJar http.CookieJar,
 	transport http.RoundTripper,
-	poolSize int,
+	panicHandler async.PanicHandler,
 ) []proton.Option {
-	return defaultAPIOptions(apiURL, version, cookieJar, transport, poolSize)
+	return defaultAPIOptions(apiURL, version, cookieJar, transport, panicHandler)
 }

internal/bridge/api_qa.go

@@ -1,4 +1,4 @@
-// Copyright (c) 2023 Proton AG
+// Copyright (c) 2025 Proton AG
 //
 // This file is part of Proton Mail Bridge.
 //
@@ -15,15 +15,17 @@
 // You should have received a copy of the GNU General Public License
 // along with Proton Mail Bridge.  If not, see <https://www.gnu.org/licenses/>.
 
-//go:build build_qa
+//go:build build_qa || test_integration
 
 package bridge
 
 import (
+	"crypto/tls"
 	"net/http"
 	"os"
 
 	"github.com/Masterminds/semver/v3"
+	"github.com/ProtonMail/gluon/async"
 	"github.com/ProtonMail/go-proton-api"
 )
 
@@ -33,9 +35,17 @@ func newAPIOptions(
 	version *semver.Version,
 	cookieJar http.CookieJar,
 	transport http.RoundTripper,
-	poolSize int,
+	panicHandler async.PanicHandler,
 ) []proton.Option {
-	opt := defaultAPIOptions(apiURL, version, cookieJar, transport, poolSize)
+
+	if allow := os.Getenv("BRIDGE_ALLOW_PROXY"); allow != "" {
+		transport = &http.Transport{
+			Proxy:           http.ProxyFromEnvironment,
+			TLSClientConfig: &tls.Config{InsecureSkipVerify: true},
+		}
+	}
+
+	opt := defaultAPIOptions(apiURL, version, cookieJar, transport, panicHandler)
 
 	if host := os.Getenv("BRIDGE_API_HOST"); host != "" {
 		opt = append(opt, proton.WithHostURL(host))

internal/bridge/bridge.go

@@ -1,4 +1,4 @@
-// Copyright (c) 2023 Proton AG
+// Copyright (c) 2025 Proton AG
 //
 // This file is part of Proton Mail Bridge.
 //
@@ -23,31 +23,45 @@ import (
 	"crypto/tls"
 	"errors"
 	"fmt"
-	"net"
 	"net/http"
+	"os"
+	"regexp"
+	"runtime"
+	"strings"
 	"sync"
 	"time"
 
 	"github.com/Masterminds/semver/v3"
-	"github.com/ProtonMail/gluon"
+	"github.com/ProtonMail/gluon/async"
 	imapEvents "github.com/ProtonMail/gluon/events"
+	"github.com/ProtonMail/gluon/imap"
 	"github.com/ProtonMail/gluon/reporter"
 	"github.com/ProtonMail/gluon/watcher"
 	"github.com/ProtonMail/go-proton-api"
-	"github.com/ProtonMail/proton-bridge/v3/internal/async"
 	"github.com/ProtonMail/proton-bridge/v3/internal/constants"
 	"github.com/ProtonMail/proton-bridge/v3/internal/events"
 	"github.com/ProtonMail/proton-bridge/v3/internal/focus"
+	"github.com/ProtonMail/proton-bridge/v3/internal/identifier"
 	"github.com/ProtonMail/proton-bridge/v3/internal/safe"
 	"github.com/ProtonMail/proton-bridge/v3/internal/sentry"
+	"github.com/ProtonMail/proton-bridge/v3/internal/services/imapsmtpserver"
+	"github.com/ProtonMail/proton-bridge/v3/internal/services/notifications"
+	"github.com/ProtonMail/proton-bridge/v3/internal/services/observability"
+	"github.com/ProtonMail/proton-bridge/v3/internal/services/syncservice"
+	"github.com/ProtonMail/proton-bridge/v3/internal/telemetry"
+	"github.com/ProtonMail/proton-bridge/v3/internal/unleash"
+	"github.com/ProtonMail/proton-bridge/v3/internal/updater"
 	"github.com/ProtonMail/proton-bridge/v3/internal/user"
 	"github.com/ProtonMail/proton-bridge/v3/internal/vault"
+	"github.com/ProtonMail/proton-bridge/v3/pkg/keychain"
 	"github.com/bradenaw/juniper/xslices"
-	"github.com/emersion/go-smtp"
+	"github.com/elastic/go-sysinfo/types"
 	"github.com/go-resty/resty/v2"
 	"github.com/sirupsen/logrus"
 )
 
+var usernameChangeRegex = regexp.MustCompile(`^/Users/([^/]+)/`)
+
 type Bridge struct {
 	// vault holds bridge-specific data, such as preferences and known users (authorized or not).
 	vault *vault.Vault
@@ -59,30 +73,31 @@ type Bridge struct {
 	// api manages user API clients.
 	api        *proton.Manager
 	proxyCtl   ProxyController
-	identifier Identifier
+	identifier identifier.Identifier
 
 	// tlsConfig holds the bridge TLS config used by the IMAP and SMTP servers.
 	tlsConfig *tls.Config
 
 	// imapServer is the bridge's IMAP server.
-	imapServer   *gluon.Server
-	imapListener net.Listener
 	imapEventCh chan imapEvents.Event
 
-	// smtpServer is the bridge's SMTP server.
-	smtpServer   *smtp.Server
-	smtpListener net.Listener
-
 	// updater is the bridge's updater.
 	updater         Updater
+	installChLegacy chan installJobLegacy
 	installCh       chan installJob
 
+	// heartbeat is the telemetry heartbeat for metrics.
+	heartbeat *heartBeatState
+
 	// curVersion is the current version of the bridge,
 	// newVersion is the version that was installed by the updater.
 	curVersion     *semver.Version
 	newVersion     *semver.Version
 	newVersionLock safe.RWMutex
 
+	// keychains is the utils that own usable keychains found in the OS.
+	keychains *keychain.List
+
 	// focusService is used to raise the bridge window when needed.
 	focusService *focus.Service
 
@@ -92,8 +107,8 @@ type Bridge struct {
 	// locator is the bridge's locator.
 	locator Locator
 
-	// crashHandler
-	crashHandler async.PanicHandler
+	// panicHandler
+	panicHandler async.PanicHandler
 
 	// reporter
 	reporter reporter.Reporter
@@ -124,39 +139,60 @@ type Bridge struct {
 
 	// goUpdate triggers a check/install of updates.
 	goUpdate func()
+
+	serverManager *imapsmtpserver.Service
+	syncService   *syncservice.Service
+
+	// unleashService is responsible for polling the feature flags and caching
+	unleashService *unleash.Service
+
+	// observabilityService is responsible for handling calls to the observability system
+	observabilityService *observability.Service
+
+	// notificationStore is used for notification deduplication
+	notificationStore *notifications.Store
+
+	// getHostVersion primarily used for testing the update logic - it should return an OS version
+	getHostVersion func(host types.Host) string
 }
 
+var logPkg = logrus.WithField("pkg", "bridge") //nolint:gochecknoglobals
+
 // New creates a new bridge.
-func New( //nolint:funlen
+func New(
 	locator Locator, // the locator to provide paths to store data
 	vault *vault.Vault, // the bridge's encrypted data store
 	autostarter Autostarter, // the autostarter to manage autostart settings
 	updater Updater, // the updater to fetch and install updates
 	curVersion *semver.Version, // the current version of the bridge
+	keychains *keychain.List, // usable keychains
 
 	apiURL string, // the URL of the API to use
 	cookieJar http.CookieJar, // the cookie jar to use
-	identifier Identifier, // the identifier to keep track of the user agent
+	identifier identifier.Identifier, // the identifier to keep track of the user agent
 	tlsReporter TLSReporter, // the TLS reporter to report TLS errors
 	roundTripper http.RoundTripper, // the round tripper to use for API requests
 	proxyCtl ProxyController, // the DoH controller
-	crashHandler async.PanicHandler,
+	panicHandler async.PanicHandler,
 	reporter reporter.Reporter,
+	uidValidityGenerator imap.UIDValidityGenerator,
+	heartBeatManager telemetry.HeartbeatManager,
 
 	logIMAPClient, logIMAPServer bool, // whether to log IMAP client/server activity
 	logSMTP bool, // whether to log SMTP activity
 ) (*Bridge, <-chan events.Event, error) {
 	// api is the user's API manager.
-	api := proton.New(newAPIOptions(apiURL, curVersion, cookieJar, roundTripper, vault.SyncAttPool())...)
+	api := proton.New(newAPIOptions(apiURL, curVersion, cookieJar, roundTripper, panicHandler)...)
 
 	// tasks holds all the bridge's background tasks.
-	tasks := async.NewGroup(context.Background(), crashHandler)
+	tasks := async.NewGroup(context.Background(), panicHandler)
 
 	// imapEventCh forwards IMAP events from gluon instances to the bridge for processing.
 	imapEventCh := make(chan imapEvents.Event)
 
 	// bridge is the bridge.
 	bridge, err := newBridge(
+		context.Background(),
 		tasks,
 		imapEventCh,
 
@@ -165,12 +201,15 @@ func New( //nolint:funlen
 		autostarter,
 		updater,
 		curVersion,
-		crashHandler,
+		keychains,
+		panicHandler,
 		reporter,
 
 		api,
 		identifier,
 		proxyCtl,
+		uidValidityGenerator,
+		heartBeatManager,
 		logIMAPClient, logIMAPServer, logSMTP,
 	)
 	if err != nil {
@@ -185,23 +224,11 @@ func New( //nolint:funlen
 		return nil, nil, fmt.Errorf("failed to initialize bridge: %w", err)
 	}
 
-	// Start serving IMAP.
-	if err := bridge.serveIMAP(); err != nil {
-		logrus.WithError(err).Error("IMAP error")
-		bridge.PushError(ErrServeIMAP)
-	}
-
-	// Start serving SMTP.
-	if err := bridge.serveSMTP(); err != nil {
-		logrus.WithError(err).Error("SMTP error")
-		bridge.PushError(ErrServeSMTP)
-	}
-
 	return bridge, eventCh, nil
 }
 
-// nolint:funlen
 func newBridge(
+	ctx context.Context,
 	tasks *async.Group,
 	imapEventCh chan imapEvents.Event,
 
@@ -210,12 +237,15 @@ func newBridge(
 	autostarter Autostarter,
 	updater Updater,
 	curVersion *semver.Version,
-	crashHandler async.PanicHandler,
+	keychains *keychain.List,
+	panicHandler async.PanicHandler,
 	reporter reporter.Reporter,
 
 	api *proton.Manager,
-	identifier Identifier,
+	identifier identifier.Identifier,
 	proxyCtl ProxyController,
+	uidValidityGenerator imap.UIDValidityGenerator,
+	heartbeatManager telemetry.HeartbeatManager,
 
 	logIMAPClient, logIMAPServer, logSMTP bool,
 ) (*Bridge, error) {
@@ -224,16 +254,6 @@ func newBridge(
 		return nil, fmt.Errorf("failed to load TLS config: %w", err)
 	}
 
-	gluonCacheDir, err := getGluonDir(vault)
-	if err != nil {
-		return nil, fmt.Errorf("failed to get Gluon directory: %w", err)
-	}
-
-	gluonDataDir, err := locator.ProvideGluonDataPath()
-	if err != nil {
-		return nil, fmt.Errorf("failed to get Gluon Database directory: %w", err)
-	}
-
 	firstStart := vault.GetFirstStart()
 	if err := vault.SetFirstStart(false); err != nil {
 		return nil, fmt.Errorf("failed to save first start indicator: %w", err)
@@ -244,26 +264,17 @@ func newBridge(
 		return nil, fmt.Errorf("failed to save last version indicator: %w", err)
 	}
 
-	imapServer, err := newIMAPServer(
-		gluonCacheDir,
-		gluonDataDir,
-		curVersion,
-		tlsConfig,
-		reporter,
-		logIMAPClient,
-		logIMAPServer,
-		imapEventCh,
-		tasks,
-	)
-	if err != nil {
-		return nil, fmt.Errorf("failed to create IMAP server: %w", err)
-	}
+	identifier.SetClientString(vault.GetLastUserAgent())
 
-	focusService, err := focus.NewService(curVersion)
+	focusService, err := focus.NewService(locator, curVersion, panicHandler)
 	if err != nil {
 		return nil, fmt.Errorf("failed to create focus service: %w", err)
 	}
 
+	unleashService := unleash.NewBridgeService(ctx, api, locator, panicHandler)
+
+	observabilityService := observability.NewService(ctx, panicHandler)
+
 	bridge := &Bridge{
 		vault: vault,
 
@@ -275,19 +286,23 @@ func newBridge(
 		identifier: identifier,
 
 		tlsConfig:   tlsConfig,
-		imapServer:  imapServer,
 		imapEventCh: imapEventCh,
 
 		updater:         updater,
+		installChLegacy: make(chan installJobLegacy),
 		installCh:       make(chan installJob),
 
 		curVersion:     curVersion,
 		newVersion:     curVersion,
 		newVersionLock: safe.NewRWMutex(),
 
-		crashHandler: crashHandler,
+		keychains: keychains,
+
+		panicHandler: panicHandler,
 		reporter:     reporter,
 
+		heartbeat: newHeartBeatState(ctx, panicHandler),
+
 		focusService: focusService,
 		autostarter:  autostarter,
 		locator:      locator,
@@ -300,14 +315,50 @@ func newBridge(
 		lastVersion: lastVersion,
 
 		tasks:       tasks,
+		syncService: syncservice.NewService(panicHandler, observabilityService),
+
+		unleashService: unleashService,
+
+		observabilityService: observabilityService,
+
+		notificationStore: notifications.NewStore(locator.ProvideNotificationsCachePath),
+
+		getHostVersion: func(host types.Host) string { return host.Info().OS.Version },
 	}
 
-	bridge.smtpServer = newSMTPServer(bridge, tlsConfig, logSMTP)
+	bridge.serverManager = imapsmtpserver.NewService(context.Background(),
+		&bridgeSMTPSettings{b: bridge},
+		&bridgeIMAPSettings{b: bridge},
+		&bridgeEventPublisher{b: bridge},
+		panicHandler,
+		reporter,
+		uidValidityGenerator,
+		&bridgeIMAPSMTPTelemetry{b: bridge},
+		observabilityService,
+	)
+
+	// Check whether username has changed and correct (macOS only)
+	bridge.verifyUsernameChange()
+
+	if err := bridge.serverManager.Init(context.Background(), bridge.tasks, &bridgeEventSubscription{b: bridge}); err != nil {
+		return nil, err
+	}
+
+	if heartbeatManager == nil {
+		bridge.heartbeat.init(bridge, bridge)
+	} else {
+		bridge.heartbeat.init(bridge, heartbeatManager)
+	}
+
+	bridge.syncService.Run()
+
+	bridge.unleashService.Run()
+
+	bridge.observabilityService.Run(bridge)
 
 	return bridge, nil
 }
 
-// nolint:funlen
 func (bridge *Bridge) init(tlsReporter TLSReporter) error {
 	// Enable or disable the proxy at startup.
 	if bridge.vault.GetProxyAllowed() {
@@ -318,7 +369,7 @@ func (bridge *Bridge) init(tlsReporter TLSReporter) error {
 
 	// Handle connection up/down events.
 	bridge.api.AddStatusObserver(func(status proton.Status) {
-		logrus.Info("API status changed: ", status)
+		logPkg.Info("API status changed: ", status)
 
 		switch {
 		case status == proton.StatusUp:
@@ -333,7 +384,7 @@ func (bridge *Bridge) init(tlsReporter TLSReporter) error {
 
 	// If any call returns a bad version code, we need to update.
 	bridge.api.AddErrorHandler(proton.AppVersionBadCode, func() {
-		logrus.Warn("App version is bad")
+		logPkg.Warn("App version is bad")
 		bridge.publish(events.UpdateForced{})
 	})
 
@@ -346,7 +397,7 @@ func (bridge *Bridge) init(tlsReporter TLSReporter) error {
 	// Log all manager API requests (client requests are logged separately).
 	bridge.api.AddPostRequestHook(func(_ *resty.Client, r *resty.Response) error {
 		if _, ok := proton.ClientIDFromContext(r.Request.Context()); !ok {
-			logrus.Infof("[MANAGER] %v: %v %v", r.Status(), r.Request.Method, r.Request.URL)
+			logrus.WithField("pkg", "gpa/manager").Infof("%v: %v %v", r.Status(), r.Request.Method, r.Request.URL)
 		}
 
 		return nil
@@ -355,7 +406,7 @@ func (bridge *Bridge) init(tlsReporter TLSReporter) error {
 	// Publish a TLS issue event if a TLS issue is encountered.
 	bridge.tasks.Once(func(ctx context.Context) {
 		async.RangeContext(ctx, tlsReporter.GetTLSIssueCh(), func(struct{}) {
-			logrus.Warn("TLS issue encountered")
+			logPkg.Warn("TLS issue encountered")
 			bridge.publish(events.TLSIssue{})
 		})
 	})
@@ -363,7 +414,7 @@ func (bridge *Bridge) init(tlsReporter TLSReporter) error {
 	// Publish a raise event if the focus service is called.
 	bridge.tasks.Once(func(ctx context.Context) {
 		async.RangeContext(ctx, bridge.focusService.GetRaiseCh(), func(struct{}) {
-			logrus.Info("Focus service requested raise")
+			logPkg.Info("Focus service requested raise")
 			bridge.publish(events.Raise{})
 		})
 	})
@@ -371,38 +422,68 @@ func (bridge *Bridge) init(tlsReporter TLSReporter) error {
 	// Handle any IMAP events that are forwarded to the bridge from gluon.
 	bridge.tasks.Once(func(ctx context.Context) {
 		async.RangeContext(ctx, bridge.imapEventCh, func(event imapEvents.Event) {
-			logrus.WithField("event", fmt.Sprintf("%T", event)).Debug("Received IMAP event")
+			logPkg.WithField("event", fmt.Sprintf("%T", event)).Debug("Received IMAP event")
 			bridge.handleIMAPEvent(event)
 		})
 	})
 
-	// Attempt to lazy load users when triggered.
+	// Attempt to load users from the vault when triggered.
 	bridge.goLoad = bridge.tasks.Trigger(func(ctx context.Context) {
 		if err := bridge.loadUsers(ctx); err != nil {
-			logrus.WithError(err).Error("Failed to load users")
+			logPkg.WithError(err).Error("Failed to load users")
 			if netErr := new(proton.NetError); !errors.As(err, &netErr) {
 				sentry.ReportError(bridge.reporter, "Failed to load users", err)
 			}
-		} else {
-			bridge.publish(events.AllUsersLoaded{})
+			return
 		}
+
+		bridge.publish(events.AllUsersLoaded{})
 	})
 	defer bridge.goLoad()
 
 	// Check for updates when triggered.
 	bridge.goUpdate = bridge.tasks.PeriodicOrTrigger(constants.UpdateCheckInterval, 0, func(ctx context.Context) {
-		logrus.Info("Checking for updates")
+		logPkg.Info("Checking for updates")
+		var versionLegacy updater.VersionInfoLegacy
+		var version updater.VersionInfo
+		var err error
+
+		useOldUpdateLogic := bridge.GetFeatureFlagValue(unleash.UpdateUseNewVersionFileStructureDisabled)
+		if useOldUpdateLogic {
+			versionLegacy, err = bridge.updater.GetVersionInfoLegacy(ctx, bridge.api, bridge.vault.GetUpdateChannel())
+		} else {
+			version, err = bridge.updater.GetVersionInfo(ctx, bridge.api)
+		}
 
-		version, err := bridge.updater.GetVersionInfo(ctx, bridge.api, bridge.vault.GetUpdateChannel())
 		if err != nil {
 			bridge.publish(events.UpdateCheckFailed{Error: err})
+			if errors.Is(err, updater.ErrVersionFileDownloadOrVerify) {
+				logPkg.WithError(err).Error("Cannot download or verify the version file")
+				if reporterErr := bridge.reporter.ReportMessageWithContext(
+					"Cannot download or verify the version file",
+					reporter.Context{"error": err},
+				); reporterErr != nil {
+					logPkg.WithError(reporterErr).Error("Failed to report version file check error")
+				}
+			}
+		} else {
+			if useOldUpdateLogic {
+				bridge.handleUpdateLegacy(versionLegacy)
 			} else {
 				bridge.handleUpdate(version)
 			}
+		}
 	})
 	defer bridge.goUpdate()
 
-	// Install updates when available.
+	// Install updates when available - based on old update logic
+	bridge.tasks.Once(func(ctx context.Context) {
+		async.RangeContext(ctx, bridge.installChLegacy, func(job installJobLegacy) {
+			bridge.installUpdateLegacy(ctx, job)
+		})
+	})
+
+	// Install updates when available - based on new update logic
 	bridge.tasks.Once(func(ctx context.Context) {
 		async.RangeContext(ctx, bridge.installCh, func(job installJob) {
 			bridge.installUpdate(ctx, job)
@@ -429,31 +510,37 @@ func (bridge *Bridge) GetErrors() []error {
 }
 
 func (bridge *Bridge) Close(ctx context.Context) {
-	logrus.Info("Closing bridge")
+	logPkg.Info("Closing bridge")
 
-	// Close the IMAP server.
-	if err := bridge.closeIMAP(ctx); err != nil {
-		logrus.WithError(err).Error("Failed to close IMAP server")
-	}
+	// Stop observability service
+	bridge.observabilityService.Stop()
 
-	// Close the SMTP server.
-	if err := bridge.closeSMTP(); err != nil {
-		logrus.WithError(err).Error("Failed to close SMTP server")
-	}
+	// Stop heart beat before closing users.
+	bridge.heartbeat.stop()
 
 	// Close all users.
-	safe.RLock(func() {
+	safe.Lock(func() {
 		for _, user := range bridge.users {
 			user.Close()
 		}
 	}, bridge.usersLock)
 
+	// Close the servers
+	if err := bridge.serverManager.CloseServers(ctx); err != nil {
+		logPkg.WithError(err).Error("Failed to close servers")
+	}
+
+	bridge.syncService.Close()
+
 	// Stop all ongoing tasks.
 	bridge.tasks.CancelAndWait()
 
 	// Close the focus service.
 	bridge.focusService.Close()
 
+	// Close the unleash service.
+	bridge.unleashService.Close()
+
 	// Close the watchers.
 	bridge.watchersLock.Lock()
 	defer bridge.watchersLock.Unlock()
@@ -469,12 +556,12 @@ func (bridge *Bridge) publish(event events.Event) {
 	bridge.watchersLock.RLock()
 	defer bridge.watchersLock.RUnlock()
 
-	logrus.WithField("event", event).Debug("Publishing event")
+	logPkg.WithField("event", event).Debug("Publishing event")
 
 	for _, watcher := range bridge.watchers {
 		if watcher.IsWatching(event) {
 			if ok := watcher.Send(event); !ok {
-				logrus.WithField("event", event).Warn("Failed to send event to watcher")
+				logPkg.WithField("event", event).Warn("Failed to send event to watcher")
 			}
 		}
 	}
@@ -484,7 +571,7 @@ func (bridge *Bridge) addWatcher(ofType ...events.Event) *watcher.Watcher[events
 	bridge.watchersLock.Lock()
 	defer bridge.watchersLock.Unlock()
 
-	watcher := watcher.New(ofType...)
+	watcher := watcher.New(bridge.panicHandler, ofType...)
 
 	bridge.watchers = append(bridge.watchers, watcher)
 
@@ -506,26 +593,14 @@ func (bridge *Bridge) remWatcher(watcher *watcher.Watcher[events.Event]) {
 	watcher.Close()
 }
 
-func (bridge *Bridge) onStatusUp(ctx context.Context) {
-	logrus.Info("Handling API status up")
-
-	safe.RLock(func() {
-		for _, user := range bridge.users {
-			user.OnStatusUp(ctx)
-		}
-	}, bridge.usersLock)
+func (bridge *Bridge) onStatusUp(_ context.Context) {
+	logPkg.Info("Handling API status up")
 
 	bridge.goLoad()
 }
 
 func (bridge *Bridge) onStatusDown(ctx context.Context) {
-	logrus.Info("Handling API status down")
-
-	safe.RLock(func() {
-		for _, user := range bridge.users {
-			user.OnStatusDown(ctx)
-		}
-	}, bridge.usersLock)
+	logPkg.Info("Handling API status down")
 
 	for backoff := time.Second; ; backoff = min(backoff*2, 30*time.Second) {
 		select {
@@ -533,10 +608,10 @@ func (bridge *Bridge) onStatusDown(ctx context.Context) {
 			return
 
 		case <-time.After(backoff):
-			logrus.Info("Pinging API")
+			logPkg.Info("Pinging API")
 
 			if err := bridge.api.Ping(ctx); err != nil {
-				logrus.WithError(err).Warn("Ping failed, API is still unreachable")
+				logPkg.WithError(err).Warn("Ping failed, API is still unreachable")
 			} else {
 				return
 			}
@@ -544,8 +619,51 @@ func (bridge *Bridge) onStatusDown(ctx context.Context) {
 	}
 }
 
+func (bridge *Bridge) Repair() {
+	var wg sync.WaitGroup
+	userIDs := bridge.GetUserIDs()
+
+	for _, userID := range userIDs {
+		logPkg.Info("Initiating repair for userID:", userID)
+
+		userInfo, err := bridge.GetUserInfo(userID)
+		if err != nil {
+			logPkg.WithError(err).Error("Failed getting user info for repair; ID:", userID)
+			continue
+		}
+
+		if userInfo.State != Connected {
+			logPkg.Info("User is not connected. Repair will be executed on following successful log in.", userID)
+			if err := bridge.vault.GetUser(userID, func(user *vault.User) {
+				if err := user.SetShouldSync(true); err != nil {
+					logPkg.WithError(err).Error("Failed setting vault should sync for user:", userID)
+				}
+			}); err != nil {
+				logPkg.WithError(err).Error("Unable to get user vault when scheduling repair:", userID)
+			}
+			continue
+		}
+
+		bridgeUser, ok := bridge.users[userID]
+		if !ok {
+			logPkg.Info("UserID does not exist in bridge user map", userID)
+			continue
+		}
+
+		wg.Add(1)
+		go func(userID string) {
+			defer wg.Done()
+			if err = bridgeUser.TriggerRepair(); err != nil {
+				logPkg.WithError(err).Error("Failed re-syncing IMAP for userID", userID)
+			}
+		}(userID)
+	}
+
+	wg.Wait()
+}
+
 func loadTLSConfig(vault *vault.Vault) (*tls.Config, error) {
-	cert, err := tls.X509KeyPair(vault.GetBridgeTLSCert(), vault.GetBridgeTLSKey())
+	cert, err := tls.X509KeyPair(vault.GetBridgeTLSCert())
 	if err != nil {
 		return nil, err
 	}
@@ -556,28 +674,113 @@ func loadTLSConfig(vault *vault.Vault) (*tls.Config, error) {
 	}, nil
 }
 
-func newListener(port int, useTLS bool, tlsConfig *tls.Config) (net.Listener, error) {
-	if useTLS {
-		tlsListener, err := tls.Listen("tcp", fmt.Sprintf("%v:%v", constants.Host, port), tlsConfig)
-		if err != nil {
-			return nil, err
-		}
-
-		return tlsListener, nil
-	}
-
-	netListener, err := net.Listen("tcp", fmt.Sprintf("%v:%v", constants.Host, port))
-	if err != nil {
-		return nil, err
-	}
-
-	return netListener, nil
+func (bridge *Bridge) HasAPIConnection() bool {
+	return bridge.api.GetStatus() == proton.StatusUp
 }
 
-func min(a, b time.Duration) time.Duration {
-	if a < b {
-		return a
+// verifyUsernameChange - works only on macOS
+// it attempts to check whether a username change has taken place by comparing the gluon DB path (which is static and provided by bridge)
+// to the gluon Cache path - which can be modified by the user and is stored in the vault;
+// if a username discrepancy is detected, and the cache folder does not exist with the "old" username
+// then we verify whether the gluon cache exists using the "new" username (provided by the DB path in this case)
+// if so we modify the cache directory in the user vault.
+func (bridge *Bridge) verifyUsernameChange() {
+	if runtime.GOOS != "darwin" {
+		return
 	}
 
-	return b
+	gluonDBPath, err := bridge.GetGluonDataDir()
+	if err != nil {
+		logPkg.WithError(err).Error("Failed to get gluon db path")
+		return
+	}
+
+	gluonCachePath := bridge.GetGluonCacheDir()
+	// If the cache folder exists even on another user account or is in `/Users/Shared` we would still be able to access it
+	// though it depends on the permissions; this is an edge-case.
+	if _, err := os.Stat(gluonCachePath); err == nil {
+		return
+	}
+
+	newCacheDir := GetUpdatedCachePath(gluonDBPath, gluonCachePath)
+	if newCacheDir == "" {
+		return
+	}
+
+	if _, err := os.Stat(newCacheDir); err == nil {
+		logPkg.Info("Username change detected. Trying to restore gluon cache directory")
+		if err = bridge.vault.SetGluonDir(newCacheDir); err != nil {
+			logPkg.WithError(err).Error("Failed to restore gluon cache directory")
+			return
+		}
+		logPkg.Info("Successfully restored gluon cache directory")
+	}
+}
+
+func GetUpdatedCachePath(gluonDBPath, gluonCachePath string) string {
+	// If gluon cache is moved to an external drive; regex find will fail; as is expected
+	cachePathMatches := usernameChangeRegex.FindStringSubmatch(gluonCachePath)
+	if cachePathMatches == nil || len(cachePathMatches) < 2 {
+		return ""
+	}
+
+	cacheUsername := cachePathMatches[1]
+	dbPathMatches := usernameChangeRegex.FindStringSubmatch(gluonDBPath)
+	if dbPathMatches == nil || len(dbPathMatches) < 2 {
+		return ""
+	}
+
+	dbUsername := dbPathMatches[1]
+	if cacheUsername == dbUsername {
+		return ""
+	}
+
+	return strings.Replace(gluonCachePath, "/Users/"+cacheUsername+"/", "/Users/"+dbUsername+"/", 1)
+}
+
+func (bridge *Bridge) GetFeatureFlagValue(key string) bool {
+	return bridge.unleashService.GetFlagValue(key)
+}
+
+func (bridge *Bridge) PushObservabilityMetric(metric proton.ObservabilityMetric) {
+	bridge.observabilityService.AddMetrics(metric)
+}
+
+func (bridge *Bridge) PushDistinctObservabilityMetrics(errType observability.DistinctionErrorTypeEnum, metrics ...proton.ObservabilityMetric) {
+	bridge.observabilityService.AddDistinctMetrics(errType, metrics...)
+}
+
+func (bridge *Bridge) ModifyObservabilityHeartbeatInterval(duration time.Duration) {
+	bridge.observabilityService.ModifyHeartbeatInterval(duration)
+}
+
+func (bridge *Bridge) ReportMessageWithContext(message string, messageCtx reporter.Context) {
+	if err := bridge.reporter.ReportMessageWithContext(message, messageCtx); err != nil {
+		logPkg.WithFields(logrus.Fields{
+			"err":           err,
+			"sentryMessage": message,
+			"messageCtx":    messageCtx,
+		}).Info("Error occurred when sending Report to Sentry")
+	}
+}
+
+// GetUsers is only used for testing purposes.
+func (bridge *Bridge) GetUsers() map[string]*user.User {
+	return bridge.users
+}
+
+// SetCurrentVersionTest - sets the current version of bridge; should only be used for tests.
+func (bridge *Bridge) SetCurrentVersionTest(version *semver.Version) {
+	bridge.curVersion = version
+	bridge.newVersion = version
+}
+
+// SetHostVersionGetterTest - sets the OS version helper func; only used for testing.
+func (bridge *Bridge) SetHostVersionGetterTest(fn func(host types.Host) string) {
+	bridge.getHostVersion = fn
+}
+
+// SetRolloutPercentageTest - sets the rollout percentage; should only be used for testing.
+func (bridge *Bridge) SetRolloutPercentageTest(rollout float64) error {
+	return bridge.vault.SetUpdateRollout(rollout)
 }

internal/bridge/bridge_test.go

@@ -1,4 +1,4 @@
-// Copyright (c) 2023 Proton AG
+// Copyright (c) 2025 Proton AG
 //
 // This file is part of Proton Mail Bridge.
 //
@@ -21,14 +21,18 @@ import (
 	"context"
 	"crypto/tls"
 	"fmt"
+	"net"
 	"net/http"
 	"os"
 	"path/filepath"
+	"strings"
 	"sync"
 	"testing"
 	"time"
 
 	"github.com/Masterminds/semver/v3"
+	"github.com/ProtonMail/gluon/async"
+	"github.com/ProtonMail/gluon/imap"
 	"github.com/ProtonMail/go-proton-api"
 	"github.com/ProtonMail/go-proton-api/server"
 	"github.com/ProtonMail/go-proton-api/server/backend"
@@ -40,14 +44,20 @@ import (
 	"github.com/ProtonMail/proton-bridge/v3/internal/events"
 	"github.com/ProtonMail/proton-bridge/v3/internal/focus"
 	"github.com/ProtonMail/proton-bridge/v3/internal/locations"
+	"github.com/ProtonMail/proton-bridge/v3/internal/services/imapsmtpserver"
+	"github.com/ProtonMail/proton-bridge/v3/internal/unleash"
 	"github.com/ProtonMail/proton-bridge/v3/internal/updater"
 	"github.com/ProtonMail/proton-bridge/v3/internal/user"
 	"github.com/ProtonMail/proton-bridge/v3/internal/useragent"
 	"github.com/ProtonMail/proton-bridge/v3/internal/vault"
+	"github.com/ProtonMail/proton-bridge/v3/pkg/keychain"
 	"github.com/ProtonMail/proton-bridge/v3/tests"
 	"github.com/bradenaw/juniper/xslices"
-	"github.com/emersion/go-imap/client"
+	imapid "github.com/emersion/go-imap-id"
+	"github.com/emersion/go-sasl"
+	"github.com/emersion/go-smtp"
 	"github.com/stretchr/testify/require"
+	"go.uber.org/goleak"
 )
 
 var (
@@ -67,7 +77,7 @@ func init() {
 
 func TestBridge_ConnStatus(t *testing.T) {
 	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, vaultKey []byte) {
-		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, vaultKey, func(bridge *bridge.Bridge, mocks *bridge.Mocks) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, vaultKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
 			// Get a stream of connection status events.
 			eventCh, done := bridge.GetEvents(events.ConnStatusUp{}, events.ConnStatusDown{})
 			defer done()
@@ -116,13 +126,16 @@ func TestBridge_TLSIssue(t *testing.T) {
 
 func TestBridge_Focus(t *testing.T) {
 	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, vaultKey []byte) {
-		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, vaultKey, func(bridge *bridge.Bridge, mocks *bridge.Mocks) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, vaultKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
 			// Get a stream of TLS issue events.
 			raiseCh, done := bridge.GetEvents(events.Raise{})
 			defer done()
 
+			settingsFolder, err := locator.ProvideSettingsPath()
+			require.NoError(t, err)
+
 			// Simulate a focus event.
-			focus.TryRaise()
+			focus.TryRaise(settingsFolder)
 
 			// Wait for the event.
 			require.IsType(t, events.Raise{}, <-raiseCh)
@@ -144,7 +157,7 @@ func TestBridge_UserAgent(t *testing.T) {
 			calls = append(calls, call)
 		})
 
-		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, vaultKey, func(bridge *bridge.Bridge, mocks *bridge.Mocks) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, vaultKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
 			// Set the platform to something other than the default.
 			bridge.SetCurrentPlatform("platform")
 
@@ -164,6 +177,174 @@ func TestBridge_UserAgent(t *testing.T) {
 	})
 }
 
+func TestBridge_UserAgent_Persistence(t *testing.T) {
+	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, vaultKey []byte) {
+		otherPassword := []byte("bar")
+		otherUser := "foo"
+		_, _, err := s.CreateUser(otherUser, otherPassword)
+		require.NoError(t, err)
+
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, vaultKey, func(b *bridge.Bridge, _ *bridge.Mocks) {
+			currentUserAgent := b.GetCurrentUserAgent()
+			require.Contains(t, currentUserAgent, useragent.DefaultUserAgent)
+
+			require.NoError(t, getErr(b.LoginFull(ctx, otherUser, otherPassword, nil, nil)))
+
+			imapClient, err := eventuallyDial(fmt.Sprintf("%v:%v", constants.Host, b.GetIMAPPort()))
+			require.NoError(t, err)
+			defer func() { _ = imapClient.Logout() }()
+
+			idClient := imapid.NewClient(imapClient)
+
+			// Set IMAP ID before Login to have the value capture in the Login API Call.
+			_, err = idClient.ID(imapid.ID{
+				imapid.FieldName:    "MyFancyClient",
+				imapid.FieldVersion: "0.1.2",
+			})
+
+			require.NoError(t, err)
+
+			// Login the user.
+			_, err = b.LoginFull(context.Background(), username, password, nil, nil)
+			require.NoError(t, err)
+
+			// Assert that the user agent then contains the platform.
+			require.Contains(t, b.GetCurrentUserAgent(), "MyFancyClient/0.1.2")
+		})
+
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, vaultKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
+			currentUserAgent := bridge.GetCurrentUserAgent()
+			require.Contains(t, currentUserAgent, "MyFancyClient/0.1.2")
+		})
+	})
+}
+
+func TestBridge_UserAgentFromUnknownClient(t *testing.T) {
+	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, vaultKey []byte) {
+		otherPassword := []byte("bar")
+		otherUser := "foo"
+		_, _, err := s.CreateUser(otherUser, otherPassword)
+		require.NoError(t, err)
+
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, vaultKey, func(b *bridge.Bridge, _ *bridge.Mocks) {
+			currentUserAgent := b.GetCurrentUserAgent()
+			require.Contains(t, currentUserAgent, useragent.DefaultUserAgent)
+
+			userID, err := b.LoginFull(context.Background(), username, password, nil, nil)
+			require.NoError(t, err)
+
+			imapClient, err := eventuallyDial(fmt.Sprintf("%v:%v", constants.Host, b.GetIMAPPort()))
+			require.NoError(t, err)
+			defer func() { _ = imapClient.Logout() }()
+
+			info, err := b.GetUserInfo(userID)
+			require.NoError(t, err)
+			require.True(t, info.State == bridge.Connected)
+
+			require.NoError(t, imapClient.Login(info.Addresses[0], string(info.BridgePass)))
+
+			currentUserAgent = b.GetCurrentUserAgent()
+			require.Contains(t, currentUserAgent, "UnknownClient/0.0.1")
+		})
+	})
+}
+
+func TestBridge_UserAgentFromSMTPClient(t *testing.T) {
+	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, vaultKey []byte) {
+		otherPassword := []byte("bar")
+		otherUser := "foo"
+		_, _, err := s.CreateUser(otherUser, otherPassword)
+		require.NoError(t, err)
+
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, vaultKey, func(b *bridge.Bridge, _ *bridge.Mocks) {
+			currentUserAgent := b.GetCurrentUserAgent()
+			require.Contains(t, currentUserAgent, useragent.DefaultUserAgent)
+
+			userID, err := b.LoginFull(context.Background(), username, password, nil, nil)
+			require.NoError(t, err)
+
+			client, err := smtp.Dial(net.JoinHostPort(constants.Host, fmt.Sprint(b.GetSMTPPort())))
+			require.NoError(t, err)
+			defer client.Close() //nolint:errcheck
+
+			info, err := b.GetUserInfo(userID)
+			require.NoError(t, err)
+			require.True(t, info.State == bridge.Connected)
+
+			// Upgrade to TLS.
+			require.NoError(t, client.StartTLS(&tls.Config{InsecureSkipVerify: true}))
+			require.NoError(t, client.Auth(sasl.NewLoginClient(
+				info.Addresses[0],
+				string(info.BridgePass)),
+			))
+
+			require.Eventually(t, func() bool {
+				currentUserAgent = b.GetCurrentUserAgent()
+
+				return strings.Contains(currentUserAgent, "UnknownClient/0.0.1")
+			}, time.Minute, 5*time.Second)
+		})
+	})
+}
+
+func TestBridge_UserAgentFromIMAPID(t *testing.T) {
+	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, vaultKey []byte) {
+		var (
+			calls []server.Call
+			lock  sync.Mutex
+		)
+
+		s.AddCallWatcher(func(call server.Call) {
+			lock.Lock()
+			defer lock.Unlock()
+
+			calls = append(calls, call)
+		})
+
+		otherPassword := []byte("bar")
+		otherUser := "foo"
+		_, _, err := s.CreateUser(otherUser, otherPassword)
+		require.NoError(t, err)
+
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, vaultKey, func(b *bridge.Bridge, _ *bridge.Mocks) {
+			require.NoError(t, getErr(b.LoginFull(ctx, otherUser, otherPassword, nil, nil)))
+
+			imapClient, err := eventuallyDial(fmt.Sprintf("%v:%v", constants.Host, b.GetIMAPPort()))
+			require.NoError(t, err)
+			defer func() { _ = imapClient.Logout() }()
+
+			idClient := imapid.NewClient(imapClient)
+
+			// Set IMAP ID before Login to have the value capture in the Login API Call.
+			_, err = idClient.ID(imapid.ID{
+				imapid.FieldName:    "MyFancyClient",
+				imapid.FieldVersion: "0.1.2",
+			})
+
+			require.NoError(t, err)
+
+			// Login the user.
+			userID, err := b.LoginFull(context.Background(), username, password, nil, nil)
+			require.NoError(t, err)
+
+			info, err := b.GetUserInfo(userID)
+			require.NoError(t, err)
+			require.True(t, info.State == bridge.Connected)
+
+			require.NoError(t, imapClient.Login(info.Addresses[0], string(info.BridgePass)))
+
+			lock.Lock()
+			defer lock.Unlock()
+
+			userAgent := calls[len(calls)-1].RequestHeader.Get("User-Agent")
+
+			// Assert that the user agent was sent to the API.
+			require.Contains(t, userAgent, b.GetCurrentUserAgent())
+			require.Contains(t, userAgent, "MyFancyClient/0.1.2")
+		})
+	})
+}
+
 func TestBridge_Cookies(t *testing.T) {
 	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, vaultKey []byte) {
 		var (
@@ -185,13 +366,13 @@ func TestBridge_Cookies(t *testing.T) {
 		})
 
 		// Start bridge and add a user so that API assigns us a session ID via cookie.
-		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, vaultKey, func(bridge *bridge.Bridge, mocks *bridge.Mocks) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, vaultKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
 			_, err := bridge.LoginFull(context.Background(), username, password, nil, nil)
 			require.NoError(t, err)
 		})
 
 		// Start bridge again and check that it uses the same session ID.
-		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, vaultKey, func(bridge *bridge.Bridge, mocks *bridge.Mocks) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, vaultKey, func(_ *bridge.Bridge, _ *bridge.Mocks) {
 			// ...
 		})
 
@@ -203,9 +384,14 @@ func TestBridge_Cookies(t *testing.T) {
 	})
 }
 
-func TestBridge_CheckUpdate(t *testing.T) {
+func TestBridge_CheckUpdate_Legacy(t *testing.T) {
 	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, vaultKey []byte) {
+		unleash.ModifyPollPeriodAndJitter(500*time.Millisecond, 0)
+		s.PushFeatureFlag(unleash.UpdateUseNewVersionFileStructureDisabled)
+
 		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, vaultKey, func(bridge *bridge.Bridge, mocks *bridge.Mocks) {
+			// Wait for FF poll.
+			time.Sleep(600 * time.Millisecond)
 			// Disable autoupdate for this test.
 			require.NoError(t, bridge.SetAutoUpdate(false))
 
@@ -220,7 +406,7 @@ func TestBridge_CheckUpdate(t *testing.T) {
 			require.Equal(t, events.UpdateNotAvailable{}, <-noUpdateCh)
 
 			// Simulate a new version being available.
-			mocks.Updater.SetLatestVersion(v2_4_0, v2_3_0)
+			mocks.Updater.SetLatestVersionLegacy(v2_4_0, v2_3_0)
 
 			// Get a stream of update available events.
 			updateCh, done := bridge.GetEvents(events.UpdateAvailable{})
@@ -231,7 +417,7 @@ func TestBridge_CheckUpdate(t *testing.T) {
 
 			// We should receive an event indicating that an update is available.
 			require.Equal(t, events.UpdateAvailable{
-				Version: updater.VersionInfo{
+				VersionLegacy: updater.VersionInfoLegacy{
 					Version:           v2_4_0,
 					MinAuto:           v2_3_0,
 					RolloutProportion: 1.0,
@@ -243,25 +429,30 @@ func TestBridge_CheckUpdate(t *testing.T) {
 	})
 }
 
-func TestBridge_AutoUpdate(t *testing.T) {
+func TestBridge_AutoUpdate_Legacy(t *testing.T) {
 	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, vaultKey []byte) {
-		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, vaultKey, func(bridge *bridge.Bridge, mocks *bridge.Mocks) {
+		unleash.ModifyPollPeriodAndJitter(500*time.Millisecond, 0)
+		s.PushFeatureFlag(unleash.UpdateUseNewVersionFileStructureDisabled)
+
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, vaultKey, func(b *bridge.Bridge, mocks *bridge.Mocks) {
+			// Wait for FF poll.
+			time.Sleep(600 * time.Millisecond)
 			// Enable autoupdate for this test.
-			require.NoError(t, bridge.SetAutoUpdate(true))
+			require.NoError(t, b.SetAutoUpdate(true))
 
 			// Get a stream of update events.
-			updateCh, done := bridge.GetEvents(events.UpdateInstalled{})
+			updateCh, done := b.GetEvents(events.UpdateInstalled{})
 			defer done()
 
 			// Simulate a new version being available.
-			mocks.Updater.SetLatestVersion(v2_4_0, v2_3_0)
+			mocks.Updater.SetLatestVersionLegacy(v2_4_0, v2_3_0)
 
 			// Check for updates.
-			bridge.CheckForUpdates()
+			b.CheckForUpdates()
 
 			// We should receive an event indicating that the update was silently installed.
 			require.Equal(t, events.UpdateInstalled{
-				Version: updater.VersionInfo{
+				VersionLegacy: updater.VersionInfoLegacy{
 					Version:           v2_4_0,
 					MinAuto:           v2_3_0,
 					RolloutProportion: 1.0,
@@ -272,9 +463,14 @@ func TestBridge_AutoUpdate(t *testing.T) {
 	})
 }
 
-func TestBridge_ManualUpdate(t *testing.T) {
+func TestBridge_ManualUpdate_Legacy(t *testing.T) {
 	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, vaultKey []byte) {
+		unleash.ModifyPollPeriodAndJitter(500*time.Millisecond, 0)
+		s.PushFeatureFlag(unleash.UpdateUseNewVersionFileStructureDisabled)
+
 		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, vaultKey, func(bridge *bridge.Bridge, mocks *bridge.Mocks) {
+			// Wait for FF poll.
+			time.Sleep(600 * time.Millisecond)
 			// Disable autoupdate for this test.
 			require.NoError(t, bridge.SetAutoUpdate(false))
 
@@ -283,14 +479,14 @@ func TestBridge_ManualUpdate(t *testing.T) {
 			defer done()
 
 			// Simulate a new version being available, but it's too new for us.
-			mocks.Updater.SetLatestVersion(v2_4_0, v2_4_0)
+			mocks.Updater.SetLatestVersionLegacy(v2_4_0, v2_4_0)
 
 			// Check for updates.
 			bridge.CheckForUpdates()
 
 			// We should receive an event indicating an update is available, but we can't install it.
 			require.Equal(t, events.UpdateAvailable{
-				Version: updater.VersionInfo{
+				VersionLegacy: updater.VersionInfoLegacy{
 					Version:           v2_4_0,
 					MinAuto:           v2_4_0,
 					RolloutProportion: 1.0,
@@ -304,7 +500,12 @@ func TestBridge_ManualUpdate(t *testing.T) {
 
 func TestBridge_ForceUpdate(t *testing.T) {
 	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, vaultKey []byte) {
-		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, vaultKey, func(bridge *bridge.Bridge, mocks *bridge.Mocks) {
+		unleash.ModifyPollPeriodAndJitter(500*time.Millisecond, 0)
+		s.PushFeatureFlag(unleash.UpdateUseNewVersionFileStructureDisabled)
+
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, vaultKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
+			// Wait for FF poll.
+			time.Sleep(600 * time.Millisecond)
 			// Get a stream of update events.
 			updateCh, done := bridge.GetEvents(events.UpdateForced{})
 			defer done()
@@ -327,7 +528,7 @@ func TestBridge_BadVaultKey(t *testing.T) {
 		var userID string
 
 		// Login a user.
-		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, vaultKey, func(bridge *bridge.Bridge, mocks *bridge.Mocks) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, vaultKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
 			newUserID, err := bridge.LoginFull(context.Background(), username, password, nil, nil)
 			require.NoError(t, err)
 
@@ -335,17 +536,17 @@ func TestBridge_BadVaultKey(t *testing.T) {
 		})
 
 		// Start bridge with the correct vault key -- it should load the users correctly.
-		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, vaultKey, func(bridge *bridge.Bridge, mocks *bridge.Mocks) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, vaultKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
 			require.ElementsMatch(t, []string{userID}, bridge.GetUserIDs())
 		})
 
 		// Start bridge with a bad vault key, the vault will be wiped and bridge will show no users.
-		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, []byte("bad"), func(bridge *bridge.Bridge, mocks *bridge.Mocks) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, []byte("bad"), func(bridge *bridge.Bridge, _ *bridge.Mocks) {
 			require.Empty(t, bridge.GetUserIDs())
 		})
 
 		// Start bridge with a nil vault key, the vault will be wiped and bridge will show no users.
-		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, nil, func(bridge *bridge.Bridge, mocks *bridge.Mocks) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, nil, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
 			require.Empty(t, bridge.GetUserIDs())
 		})
 	})
@@ -355,7 +556,7 @@ func TestBridge_MissingGluonStore(t *testing.T) {
 	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, vaultKey []byte) {
 		var gluonDir string
 
-		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, vaultKey, func(bridge *bridge.Bridge, mocks *bridge.Mocks) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, vaultKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
 			_, err := bridge.LoginFull(context.Background(), username, password, nil, nil)
 			require.NoError(t, err)
 
@@ -370,7 +571,7 @@ func TestBridge_MissingGluonStore(t *testing.T) {
 		require.NoError(t, os.RemoveAll(gluonDir))
 
 		// Bridge starts but can't find the gluon store dir; there should be no error.
-		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, vaultKey, func(bridge *bridge.Bridge, mocks *bridge.Mocks) {
+		withBridgeWaitForServers(ctx, t, s.GetHostURL(), netCtl, locator, vaultKey, func(_ *bridge.Bridge, _ *bridge.Mocks) {
 			// ...
 		})
 	})
@@ -380,7 +581,7 @@ func TestBridge_MissingGluonDatabase(t *testing.T) {
 	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, vaultKey []byte) {
 		var gluonDir string
 
-		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, vaultKey, func(bridge *bridge.Bridge, mocks *bridge.Mocks) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, vaultKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
 			_, err := bridge.LoginFull(context.Background(), username, password, nil, nil)
 			require.NoError(t, err)
 
@@ -393,7 +594,7 @@ func TestBridge_MissingGluonDatabase(t *testing.T) {
 		require.NoError(t, os.RemoveAll(gluonDir))
 
 		// Bridge starts but can't find the gluon database dir; there should be no error.
-		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, vaultKey, func(bridge *bridge.Bridge, mocks *bridge.Mocks) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, vaultKey, func(_ *bridge.Bridge, _ *bridge.Mocks) {
 			// ...
 		})
 	})
@@ -407,7 +608,11 @@ func TestBridge_AddressWithoutKeys(t *testing.T) {
 		)
 		defer m.Close()
 
-		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, vaultKey, func(bridge *bridge.Bridge, mocks *bridge.Mocks) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, vaultKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
+			// Watch for sync finished event.
+			syncCh, done := chToType[events.Event, events.SyncFinished](bridge.GetEvents(events.SyncFinished{}))
+			defer done()
+
 			// Create a user which will have an address without keys.
 			userID, _, err := s.CreateUser("nokeys", []byte("password"))
 			require.NoError(t, err)
@@ -428,10 +633,6 @@ func TestBridge_AddressWithoutKeys(t *testing.T) {
 			// Remove the address keys.
 			require.NoError(t, s.RemoveAddressKey(userID, aliasAddrID, aliasAddr.Keys[0].ID))
 
-			// Watch for sync finished event.
-			syncCh, done := chToType[events.Event, events.SyncFinished](bridge.GetEvents(events.SyncFinished{}))
-			defer done()
-
 			// We should be able to log the user in.
 			require.NoError(t, getErr(bridge.LoginFull(context.Background(), "nokeys", []byte("password"), nil, nil)))
 			require.NoError(t, err)
@@ -483,19 +684,37 @@ func TestBridge_FactoryReset(t *testing.T) {
 
 func TestBridge_InitGluonDirectory(t *testing.T) {
 	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, vaultKey []byte) {
-		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, vaultKey, func(b *bridge.Bridge, mocks *bridge.Mocks) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, vaultKey, func(b *bridge.Bridge, _ *bridge.Mocks) {
 			configDir, err := b.GetGluonDataDir()
 			require.NoError(t, err)
 
-			_, err = os.ReadDir(bridge.ApplyGluonCachePathSuffix(b.GetGluonCacheDir()))
+			_, err = os.ReadDir(imapsmtpserver.ApplyGluonCachePathSuffix(b.GetGluonCacheDir()))
 			require.False(t, os.IsNotExist(err))
 
-			_, err = os.ReadDir(bridge.ApplyGluonConfigPathSuffix(configDir))
+			_, err = os.ReadDir(imapsmtpserver.ApplyGluonConfigPathSuffix(configDir))
 			require.False(t, os.IsNotExist(err))
 		})
 	})
 }
 
+func TestBridge_LoginFailed(t *testing.T) {
+	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, vaultKey []byte) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, vaultKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
+			failCh, done := chToType[events.Event, events.IMAPLoginFailed](bridge.GetEvents(events.IMAPLoginFailed{}))
+			defer done()
+
+			_, err := bridge.LoginFull(ctx, username, password, nil, nil)
+			require.NoError(t, err)
+
+			imapClient, err := eventuallyDial(net.JoinHostPort(constants.Host, fmt.Sprint(bridge.GetIMAPPort())))
+			require.NoError(t, err)
+
+			require.Error(t, imapClient.Login("badUser", "badPass"))
+			require.Equal(t, "badUser", (<-failCh).Username)
+		})
+	})
+}
+
 func TestBridge_ChangeCacheDirectory(t *testing.T) {
 	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, vaultKey []byte) {
 		userID, addrID, err := s.CreateUser("imap", password)
@@ -508,7 +727,7 @@ func TestBridge_ChangeCacheDirectory(t *testing.T) {
 			createNumMessages(ctx, t, c, addrID, labelID, 10)
 		})
 
-		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, vaultKey, func(b *bridge.Bridge, mocks *bridge.Mocks) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, vaultKey, func(b *bridge.Bridge, _ *bridge.Mocks) {
 			newCacheDir := t.TempDir()
 			currentCacheDir := b.GetGluonCacheDir()
 			configDir, err := b.GetGluonDataDir()
@@ -530,16 +749,16 @@ func TestBridge_ChangeCacheDirectory(t *testing.T) {
 			require.NoError(t, err)
 
 			// Old store should no more exists.
-			_, err = os.ReadDir(bridge.ApplyGluonCachePathSuffix(currentCacheDir))
+			_, err = os.ReadDir(imapsmtpserver.ApplyGluonCachePathSuffix(currentCacheDir))
 			require.True(t, os.IsNotExist(err))
 			// Database should not have changed.
-			_, err = os.ReadDir(bridge.ApplyGluonConfigPathSuffix(configDir))
+			_, err = os.ReadDir(imapsmtpserver.ApplyGluonConfigPathSuffix(configDir))
 			require.False(t, os.IsNotExist(err))
 
 			// New path should have Gluon sub-folder.
 			require.Equal(t, filepath.Join(newCacheDir, "gluon"), b.GetGluonCacheDir())
 			// And store should be inside it.
-			_, err = os.ReadDir(bridge.ApplyGluonCachePathSuffix(b.GetGluonCacheDir()))
+			_, err = os.ReadDir(imapsmtpserver.ApplyGluonCachePathSuffix(b.GetGluonCacheDir()))
 			require.False(t, os.IsNotExist(err))
 
 			// We should be able to fetch.
@@ -547,7 +766,7 @@ func TestBridge_ChangeCacheDirectory(t *testing.T) {
 			require.NoError(t, err)
 			require.True(t, info.State == bridge.Connected)
 
-			client, err := client.Dial(fmt.Sprintf("%v:%v", constants.Host, b.GetIMAPPort()))
+			client, err := eventuallyDial(fmt.Sprintf("%v:%v", constants.Host, b.GetIMAPPort()))
 			require.NoError(t, err)
 			require.NoError(t, client.Login(info.Addresses[0], string(info.BridgePass)))
 			defer func() { _ = client.Logout() }()
@@ -574,7 +793,7 @@ func TestBridge_ChangeAddressOrder(t *testing.T) {
 			createNumMessages(ctx, t, c, addrID, proton.InboxLabel, 10)
 		})
 
-		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, vaultKey, func(b *bridge.Bridge, mocks *bridge.Mocks) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, vaultKey, func(b *bridge.Bridge, _ *bridge.Mocks) {
 			// Log the user in with its first address.
 			syncCh, done := chToType[events.Event, events.SyncFinished](b.GetEvents(events.SyncFinished{}))
 			defer done()
@@ -587,7 +806,7 @@ func TestBridge_ChangeAddressOrder(t *testing.T) {
 			require.NoError(t, err)
 			require.True(t, info.State == bridge.Connected)
 
-			client, err := client.Dial(fmt.Sprintf("%v:%v", constants.Host, b.GetIMAPPort()))
+			client, err := eventuallyDial(fmt.Sprintf("%v:%v", constants.Host, b.GetIMAPPort()))
 			require.NoError(t, err)
 			require.NoError(t, client.Login(info.Addresses[0], string(info.BridgePass)))
 			defer func() { _ = client.Logout() }()
@@ -602,13 +821,13 @@ func TestBridge_ChangeAddressOrder(t *testing.T) {
 			require.NoError(t, c.OrderAddresses(ctx, proton.OrderAddressesReq{AddressIDs: []string{aliasID, addrID}}))
 		})
 
-		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, vaultKey, func(b *bridge.Bridge, mocks *bridge.Mocks) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, vaultKey, func(b *bridge.Bridge, _ *bridge.Mocks) {
 			// We should still see 10 messages in the inbox.
 			info, err := b.GetUserInfo(userID)
 			require.NoError(t, err)
 			require.True(t, info.State == bridge.Connected)
 
-			client, err := client.Dial(fmt.Sprintf("%v:%v", constants.Host, b.GetIMAPPort()))
+			client, err := eventuallyDial(fmt.Sprintf("%v:%v", constants.Host, b.GetIMAPPort()))
 			require.NoError(t, err)
 			require.NoError(t, client.Login(info.Addresses[0], string(info.BridgePass)))
 			defer func() { _ = client.Logout() }()
@@ -624,6 +843,9 @@ func TestBridge_ChangeAddressOrder(t *testing.T) {
 
 // withEnv creates the full test environment and runs the tests.
 func withEnv(t *testing.T, tests func(context.Context, *server.Server, *proton.NetCtl, bridge.Locator, []byte), opts ...server.Option) {
+	opt := goleak.IgnoreCurrent()
+	defer goleak.VerifyNone(t, opt)
+
 	server := server.New(opts...)
 	defer server.Close()
 
@@ -657,6 +879,9 @@ func withMocks(t *testing.T, tests func(*bridge.Mocks)) {
 	tests(mocks)
 }
 
+// Needs to be global to survive bridge shutdown/startup in unit tests as they happen to fast.
+var testUIDValidityGenerator = imap.DefaultEpochUIDValidityGenerator()
+
 // withBridge creates a new bridge which points to the given API URL and uses the given keychain, and closes it when done.
 func withBridgeNoMocks(
 	ctx context.Context,
@@ -667,6 +892,7 @@ func withBridgeNoMocks(
 	locator bridge.Locator,
 	vaultKey []byte,
 	tests func(*bridge.Bridge),
+	waitOnServers bool,
 ) {
 	// Bridge will disable the proxy by default at startup.
 	mocks.ProxyCtl.EXPECT().DisallowProxy()
@@ -676,7 +902,7 @@ func withBridgeNoMocks(
 	require.NoError(t, err)
 
 	// Create the vault.
-	vault, _, err := vault.New(vaultDir, t.TempDir(), vaultKey)
+	vault, _, err := vault.New(vaultDir, t.TempDir(), vaultKey, async.NoopPanicHandler{})
 	require.NoError(t, err)
 
 	// Create a new cookie jar.
@@ -692,6 +918,7 @@ func withBridgeNoMocks(
 		mocks.Autostarter,
 		mocks.Updater,
 		v2_3_0,
+		keychain.NewTestKeychainsList(),
 
 		// The API stuff.
 		apiURL,
@@ -702,6 +929,8 @@ func withBridgeNoMocks(
 		mocks.ProxyCtl,
 		mocks.CrashHandler,
 		mocks.Reporter,
+		testUIDValidityGenerator,
+		mocks.Heartbeat,
 
 		// The logging stuff.
 		os.Getenv("BRIDGE_LOG_IMAP_CLIENT") == "1",
@@ -715,8 +944,15 @@ func withBridgeNoMocks(
 	waitForEvent(t, eventCh, events.AllUsersLoaded{})
 
 	// Set random IMAP and SMTP ports for the tests.
-	require.NoError(t, bridge.SetIMAPPort(0))
-	require.NoError(t, bridge.SetSMTPPort(0))
+	require.NoError(t, bridge.SetIMAPPort(ctx, 0))
+	require.NoError(t, bridge.SetSMTPPort(ctx, 0))
+
+	if waitOnServers {
+		// Wait for bridge to start the IMAP server.
+		waitForEvent(t, eventCh, events.IMAPServerReady{})
+		// Wait for bridge to start the SMTP server.
+		waitForEvent(t, eventCh, events.SMTPServerReady{})
+	}
 
 	// Close the bridge when done.
 	defer bridge.Close(ctx)
@@ -738,11 +974,28 @@ func withBridge(
 	withMocks(t, func(mocks *bridge.Mocks) {
 		withBridgeNoMocks(ctx, t, mocks, apiURL, netCtl, locator, vaultKey, func(bridge *bridge.Bridge) {
 			tests(bridge, mocks)
-		})
+		}, false)
 	})
 }
 
-func waitForEvent[T any](t *testing.T, eventCh <-chan events.Event, wantEvent T) {
+// withBridgeWaitForServers is the same as withBridge, but it will wait until IMAP & SMTP servers are ready.
+func withBridgeWaitForServers(
+	ctx context.Context,
+	t *testing.T,
+	apiURL string,
+	netCtl *proton.NetCtl,
+	locator bridge.Locator,
+	vaultKey []byte,
+	tests func(*bridge.Bridge, *bridge.Mocks),
+) {
+	withMocks(t, func(mocks *bridge.Mocks) {
+		withBridgeNoMocks(ctx, t, mocks, apiURL, netCtl, locator, vaultKey, func(bridge *bridge.Bridge) {
+			tests(bridge, mocks)
+		}, true)
+	})
+}
+
+func waitForEvent[T any](t *testing.T, eventCh <-chan events.Event, _ T) {
 	t.Helper()
 
 	for event := range eventCh {
@@ -776,6 +1029,7 @@ func getConnectedUserIDs(t *testing.T, b *bridge.Bridge) []string {
 func chToType[In, Out any](inCh <-chan In, done func()) (<-chan Out, func()) {
 	outCh := make(chan Out)
 
+	ctx, cancel := context.WithCancel(context.Background())
 	go func() {
 		defer close(outCh)
 
@@ -785,9 +1039,116 @@ func chToType[In, Out any](inCh <-chan In, done func()) (<-chan Out, func()) {
 				panic(fmt.Sprintf("unexpected type %T", in))
 			}
 
-			outCh <- out
+			select {
+			case <-ctx.Done():
+				return
+
+			case outCh <- out:
+			}
 		}
 	}()
 
-	return outCh, done
+	return outCh, func() {
+		cancel()
+		done()
+	}
+}
+
+type eventWaiter struct {
+	evtCh  <-chan events.Event
+	cancel func()
+}
+
+func (e *eventWaiter) Done() {
+	e.cancel()
+}
+
+func (e *eventWaiter) Wait() {
+	<-e.evtCh
+}
+
+func waitForSMTPServerReady(b *bridge.Bridge) *eventWaiter {
+	evtCh, cancel := b.GetEvents(events.SMTPServerReady{})
+	return &eventWaiter{
+		evtCh:  evtCh,
+		cancel: cancel,
+	}
+}
+
+func waitForSMTPServerStopped(b *bridge.Bridge) *eventWaiter {
+	evtCh, cancel := b.GetEvents(events.SMTPServerStopped{})
+	return &eventWaiter{
+		evtCh:  evtCh,
+		cancel: cancel,
+	}
+}
+
+func waitForIMAPServerReady(b *bridge.Bridge) *eventWaiter {
+	evtCh, cancel := b.GetEvents(events.IMAPServerReady{})
+	return &eventWaiter{
+		evtCh:  evtCh,
+		cancel: cancel,
+	}
+}
+
+func waitForIMAPServerStopped(b *bridge.Bridge) *eventWaiter {
+	evtCh, cancel := b.GetEvents(events.IMAPServerStopped{})
+	return &eventWaiter{
+		evtCh:  evtCh,
+		cancel: cancel,
+	}
+}
+
+func TestBridge_GetUpdatedCachePath(t *testing.T) {
+	type TestData struct {
+		gluonDBPath    string
+		gluonCachePath string
+		shouldChange   bool
+	}
+
+	dataArr := []TestData{
+		{
+			gluonDBPath:    "/Users/test/",
+			gluonCachePath: "/Users/test/gluon",
+			shouldChange:   false,
+		}, {
+			gluonDBPath:    "/Users/test/",
+			gluonCachePath: "/Users/tester/gluon",
+			shouldChange:   true,
+		}, {
+			gluonDBPath:    "/Users/testing/",
+			gluonCachePath: "/Users/test/gluon",
+			shouldChange:   true,
+		},
+		{
+			gluonDBPath:    "/Users/testing/",
+			gluonCachePath: "/Users/test/gluon",
+			shouldChange:   true,
+		},
+		{
+			gluonDBPath:    "/Users/testing/",
+			gluonCachePath: "/Volumes/test/gluon",
+			shouldChange:   false,
+		},
+		{
+			gluonDBPath:    "/Volumes/test/",
+			gluonCachePath: "/Users/test/gluon",
+			shouldChange:   false,
+		},
+		{
+			gluonDBPath:    "/XXX/test/",
+			gluonCachePath: "/Users/test/gluon",
+			shouldChange:   false,
+		},
+		{
+			gluonDBPath:    "/XXX/test/",
+			gluonCachePath: "/YYY/test/gluon",
+			shouldChange:   false,
+		},
+	}
+
+	for _, el := range dataArr {
+		newCachePath := bridge.GetUpdatedCachePath(el.gluonDBPath, el.gluonCachePath)
+		require.Equal(t, el.shouldChange, newCachePath != "" && newCachePath != el.gluonCachePath)
+	}
 }

internal/bridge/bug_report.go

@@ -1,4 +1,4 @@
-// Copyright (c) 2023 Proton AG
+// Copyright (c) 2025 Proton AG
 //
 // This file is part of Proton Mail Bridge.
 //
@@ -18,13 +18,9 @@
 package bridge
 
 import (
-	"archive/zip"
-	"bytes"
 	"context"
+	"errors"
 	"io"
-	"os"
-	"path/filepath"
-	"sort"
 
 	"github.com/ProtonMail/go-proton-api"
 	"github.com/ProtonMail/proton-bridge/v3/internal/constants"
@@ -33,201 +29,131 @@ import (
 )
 
 const (
-	MaxTotalAttachmentSize  = 7 * (1 << 20)
-	MaxCompressedFilesCount = 6
+	DefaultMaxBugReportZipSize         = 7 * 1024 * 1024
+	DefaultMaxSessionCountForBugReport = 10
 )
 
-func (bridge *Bridge) ReportBug(ctx context.Context, osType, osVersion, description, username, email, client string, attachLogs bool) error { //nolint:funlen
-	var account string
+type ReportBugReq struct {
+	OSType      string
+	OSVersion   string
+	Title       string
+	Description string
+	Username    string
+	Email       string
+	EmailClient string
+	IncludeLogs bool
+}
 
-	if info, err := bridge.QueryUserInfo(username); err == nil {
-		account = info.Username
+func (bridge *Bridge) ReportBug(ctx context.Context, report *ReportBugReq) error {
+	if info, err := bridge.QueryUserInfo(report.Username); err == nil {
+		report.Username = info.Username
 	} else if userIDs := bridge.GetUserIDs(); len(userIDs) > 0 {
 		if err := bridge.vault.GetUser(userIDs[0], func(user *vault.User) {
-			account = user.Username()
+			report.Username = user.Username()
 		}); err != nil {
 			return err
 		}
 	}
 
-	var atts []proton.ReportBugAttachment
-
-	if attachLogs {
-		logs, err := getMatchingLogs(bridge.locator, func(filename string) bool {
-			return logging.MatchLogName(filename) && !logging.MatchStackTraceName(filename)
-		})
+	var attachments []proton.ReportBugAttachment
+	if report.IncludeLogs {
+		logs, err := bridge.CollectLogs()
 		if err != nil {
 			return err
 		}
+		attachments = append(attachments, logs)
+	}
 
-		crashes, err := getMatchingLogs(bridge.locator, func(filename string) bool {
-			return logging.MatchLogName(filename) && logging.MatchStackTraceName(filename)
-		})
-		if err != nil {
+	var firstAtt proton.ReportBugAttachment
+	if len(attachments) > 0 && report.IncludeLogs {
+		firstAtt = attachments[0]
+	}
+
+	attachmentType := proton.AttachmentTypeSync
+	if len(attachments) > 1 {
+		attachmentType = proton.AttachmentTypeAsync
+	}
+
+	token, err := bridge.createTicket(ctx, report, attachmentType, firstAtt)
+	if err != nil || token == "" {
 		return err
 	}
 
-		guiLogs, err := getMatchingLogs(bridge.locator, func(filename string) bool {
-			return logging.MatchGUILogName(filename) && !logging.MatchStackTraceName(filename)
-		})
+	// if we have a token we can append more attachment to the bugReport
+	for i, att := range attachments {
+		if i == 0 && report.IncludeLogs {
+			continue
+		}
+		err := bridge.appendComment(ctx, token, att)
 		if err != nil {
 			return err
 		}
-
-		var matchFiles []string
-
-		// Include bridge logs, up to a maximum amount.
-		matchFiles = append(matchFiles, logs[max(0, len(logs)-(MaxCompressedFilesCount/2)):]...)
-
-		// Include crash logs, up to a maximum amount.
-		matchFiles = append(matchFiles, crashes[max(0, len(crashes)-(MaxCompressedFilesCount/2)):]...)
-
-		// bridge-gui keeps just one small (~ 1kb) log file; we always include it.
-		if len(guiLogs) > 0 {
-			matchFiles = append(matchFiles, guiLogs[len(guiLogs)-1])
 	}
-
-		archive, err := zipFiles(matchFiles)
-		if err != nil {
 	return err
-		}
+}
 
-		body, err := io.ReadAll(archive)
+func (bridge *Bridge) CollectLogs() (proton.ReportBugAttachment, error) {
+	logsPath, err := bridge.locator.ProvideLogsPath()
 	if err != nil {
-			return err
+		return proton.ReportBugAttachment{}, err
 	}
 
-		atts = append(atts, proton.ReportBugAttachment{
+	buffer, err := logging.ZipLogsForBugReport(logsPath, DefaultMaxSessionCountForBugReport, DefaultMaxBugReportZipSize)
+	if err != nil {
+		return proton.ReportBugAttachment{}, err
+	}
+
+	body, err := io.ReadAll(buffer)
+	if err != nil {
+		return proton.ReportBugAttachment{}, err
+	}
+
+	return proton.ReportBugAttachment{
 		Name:     "logs.zip",
 		Filename: "logs.zip",
 		MIMEType: "application/zip",
 		Body:     body,
-		})
-	}
+	}, nil
+}
 
-	return bridge.api.ReportBug(ctx, proton.ReportBugReq{
-		OS:        osType,
-		OSVersion: osVersion,
+func (bridge *Bridge) createTicket(ctx context.Context, report *ReportBugReq,
+	asyncAttach proton.AttachmentType, att proton.ReportBugAttachment) (string, error) {
+	var attachments []proton.ReportBugAttachment
+	attachments = append(attachments, att)
+	res, err := bridge.api.ReportBug(ctx, proton.ReportBugReq{
+		OS:        report.OSType,
+		OSVersion: report.OSVersion,
 
-		Title:       "[Bridge] Bug",
-		Description: description,
+		Title:       "[Bridge] Bug - " + report.Title,
+		Description: report.Description,
 
-		Client:        client,
+		Client:        report.EmailClient,
 		ClientType:    proton.ClientTypeEmail,
 		ClientVersion: constants.AppVersion(bridge.curVersion.Original()),
 
-		Username: account,
-		Email:    email,
-	}, atts...)
+		Username: report.Username,
+		Email:    report.Email,
+
+		AsyncAttachments: asyncAttach,
+	}, attachments...)
+
+	if err != nil || asyncAttach != proton.AttachmentTypeAsync {
+		return "", err
+	}
+
+	if asyncAttach == proton.AttachmentTypeAsync && res.Token == nil {
+		return "", errors.New("no token returns for AsyncAttachments")
+	}
+
+	return *res.Token, nil
 }
 
-func max(a, b int) int {
-	if a > b {
-		return a
-	}
-
-	return b
-}
-
-func getMatchingLogs(locator Locator, filenameMatchFunc func(string) bool) (filenames []string, err error) {
-	logsPath, err := locator.ProvideLogsPath()
-	if err != nil {
-		return nil, err
-	}
-
-	files, err := os.ReadDir(logsPath)
-	if err != nil {
-		return nil, err
-	}
-
-	var matchFiles []string
-
-	for _, file := range files {
-		if filenameMatchFunc(file.Name()) {
-			matchFiles = append(matchFiles, filepath.Join(logsPath, file.Name()))
-		}
-	}
-
-	sort.Strings(matchFiles) // Sorted by timestamp: oldest first.
-
-	return matchFiles, nil
-}
-
-type limitedBuffer struct {
-	capacity int
-	buf      *bytes.Buffer
-}
-
-func newLimitedBuffer(capacity int) *limitedBuffer {
-	return &limitedBuffer{
-		capacity: capacity,
-		buf:      bytes.NewBuffer(make([]byte, 0, capacity)),
-	}
-}
-
-func (b *limitedBuffer) Write(p []byte) (n int, err error) {
-	if len(p)+b.buf.Len() > b.capacity {
-		return 0, ErrSizeTooLarge
-	}
-
-	return b.buf.Write(p)
-}
-
-func (b *limitedBuffer) Read(p []byte) (n int, err error) {
-	return b.buf.Read(p)
-}
-
-func zipFiles(filenames []string) (io.Reader, error) {
-	if len(filenames) == 0 {
-		return nil, nil
-	}
-
-	buf := newLimitedBuffer(MaxTotalAttachmentSize)
-
-	w := zip.NewWriter(buf)
-	defer w.Close() //nolint:errcheck
-
-	for _, file := range filenames {
-		if err := addFileToZip(file, w); err != nil {
-			return nil, err
-		}
-	}
-
-	if err := w.Close(); err != nil {
-		return nil, err
-	}
-
-	return buf, nil
-}
-
-func addFileToZip(filename string, writer *zip.Writer) error {
-	fileReader, err := os.Open(filepath.Clean(filename))
-	if err != nil {
-		return err
-	}
-	defer fileReader.Close() //nolint:errcheck,gosec
-
-	fileInfo, err := fileReader.Stat()
-	if err != nil {
-		return err
-	}
-
-	header, err := zip.FileInfoHeader(fileInfo)
-	if err != nil {
-		return err
-	}
-
-	header.Method = zip.Deflate
-	header.Name = filepath.Base(filename)
-
-	fileWriter, err := writer.CreateHeader(header)
-	if err != nil {
-		return err
-	}
-
-	if _, err := io.Copy(fileWriter, fileReader); err != nil {
-		return err
-	}
-
-	return fileReader.Close()
+func (bridge *Bridge) appendComment(ctx context.Context, token string, att proton.ReportBugAttachment) error {
+	var attachments []proton.ReportBugAttachment
+	attachments = append(attachments, att)
+	return bridge.api.ReportBugAttachement(ctx, proton.ReportBugAttachmentReq{
+		Product: proton.ClientTypeEmail,
+		Body:    "Comment adding attachment: " + att.Filename,
+		Token:   token,
+	}, attachments...)
 }

internal/bridge/configure.go

@@ -1,4 +1,4 @@
-// Copyright (c) 2023 Proton AG
+// Copyright (c) 2025 Proton AG
 //
 // This file is part of Proton Mail Bridge.
 //
@@ -18,6 +18,8 @@
 package bridge
 
 import (
+	"context"
+	"errors"
 	"strings"
 
 	"github.com/ProtonMail/proton-bridge/v3/internal/clientconfig"
@@ -29,10 +31,10 @@ import (
 	"github.com/sirupsen/logrus"
 )
 
-// ConfigureAppleMail configures apple mail for the given userID and address.
-// If configuring apple mail for Catalina or newer, it ensures Bridge is using SSL.
-func (bridge *Bridge) ConfigureAppleMail(userID, address string) error {
-	logrus.WithFields(logrus.Fields{
+// ConfigureAppleMail configures Apple Mail for the given userID and address.
+// If configuring Apple Mail for Catalina or newer, it ensures Bridge is using SSL.
+func (bridge *Bridge) ConfigureAppleMail(ctx context.Context, userID, address string) error {
+	logPkg.WithFields(logrus.Fields{
 		"userID":  userID,
 		"address": logging.Sensitive(address),
 	}).Info("Configuring Apple Mail")
@@ -43,20 +45,32 @@ func (bridge *Bridge) ConfigureAppleMail(userID, address string) error {
 			return ErrNoSuchUser
 		}
 
-		if address == "" {
-			address = user.Emails()[0]
+		emails := user.Emails()
+		displayNames := user.DisplayNames()
+		if (len(emails) == 0) || (len(displayNames) == 0) {
+			return errors.New("could not retrieve user address info")
 		}
 
-		username := address
-		addresses := address
+		if address == "" {
+			address = emails[0]
+		}
 
+		var username, displayName, addresses string
 		if user.GetAddressMode() == vault.CombinedMode {
-			username = user.Emails()[0]
-			addresses = strings.Join(user.Emails(), ",")
+			username = address
+			displayName = displayNames[username]
+			addresses = strings.Join(emails, ",")
+		} else {
+			username = address
+			addresses = address
+			displayName = displayNames[address]
+			if len(displayName) == 0 {
+				displayName = address
+			}
 		}
 
 		if useragent.IsCatalinaOrNewer() && !bridge.vault.GetSMTPSSL() {
-			if err := bridge.SetSMTPSSL(true); err != nil {
+			if err := bridge.SetSMTPSSL(ctx, true); err != nil {
 				return err
 			}
 		}
@@ -68,6 +82,7 @@ func (bridge *Bridge) ConfigureAppleMail(userID, address string) error {
 			bridge.vault.GetIMAPSSL(),
 			bridge.vault.GetSMTPSSL(),
 			username,
+			displayName,
 			addresses,
 			user.BridgePass(),
 		)

internal/bridge/debug.go

@@ -0,0 +1,301 @@
+// Copyright (c) 2025 Proton AG
+//
+// This file is part of Proton Mail Bridge.
+//
+// Proton Mail Bridge is free software: you can redistribute it and/or modify
+// it under the terms of the GNU General Public License as published by
+// the Free Software Foundation, either version 3 of the License, or
+// (at your option) any later version.
+//
+// Proton Mail Bridge is distributed in the hope that it will be useful,
+// but WITHOUT ANY WARRANTY; without even the implied warranty of
+// MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+// GNU General Public License for more details.
+//
+// You should have received a copy of the GNU General Public License
+// along with Proton Mail Bridge.  If not, see <https://www.gnu.org/licenses/>.
+
+package bridge
+
+import (
+	"context"
+	"fmt"
+	"io"
+	"os"
+	"path/filepath"
+
+	"github.com/ProtonMail/gluon/imap"
+	"github.com/ProtonMail/gluon/rfc822"
+	"github.com/ProtonMail/go-proton-api"
+	"github.com/ProtonMail/proton-bridge/v3/internal/user"
+	"github.com/bradenaw/juniper/iterator"
+	"github.com/bradenaw/juniper/xslices"
+	goimap "github.com/emersion/go-imap"
+	goimapclient "github.com/emersion/go-imap/client"
+	"github.com/sirupsen/logrus"
+	"golang.org/x/exp/maps"
+)
+
+type CheckClientStateResult struct {
+	MissingMessages map[string]map[string]user.DiagMailboxMessage
+}
+
+func (c *CheckClientStateResult) AddMissingMessage(userID string, message user.DiagMailboxMessage) {
+	v, ok := c.MissingMessages[userID]
+	if !ok {
+		c.MissingMessages[userID] = map[string]user.DiagMailboxMessage{message.ID: message}
+	} else {
+		v[message.ID] = message
+	}
+}
+
+// CheckClientState checks the current IMAP client reported state against the proton server state and reports
+// anything that is out of place.
+func (bridge *Bridge) CheckClientState(ctx context.Context, checkFlags bool, progressCB func(string)) (CheckClientStateResult, error) {
+	bridge.usersLock.RLock()
+	defer bridge.usersLock.RUnlock()
+
+	users := maps.Values(bridge.users)
+
+	result := CheckClientStateResult{
+		MissingMessages: make(map[string]map[string]user.DiagMailboxMessage),
+	}
+
+	for _, usr := range users {
+		if progressCB != nil {
+			progressCB(fmt.Sprintf("Checking state for user %v", usr.Name()))
+		}
+		log := logrus.WithFields(logrus.Fields{
+			"pkg":  "bridge/debug",
+			"user": usr.Name(),
+			"diag": "state-check",
+		})
+		log.Debug("Retrieving all server metadata")
+		meta, err := usr.GetDiagnosticMetadata(ctx)
+		if err != nil {
+			return result, err
+		}
+
+		success := true
+
+		if len(meta.Metadata) != len(meta.MessageIDs) {
+			log.Errorf("Metadata (%v) and message(%v) list sizes do not match", len(meta.Metadata), len(meta.MessageIDs))
+		}
+
+		log.Debug("Building state")
+		state, err := meta.BuildMailboxToMessageMap(ctx, usr)
+		if err != nil {
+			log.WithError(err).Error("Failed to build state")
+			return result, err
+		}
+
+		info, err := bridge.GetUserInfo(usr.ID())
+		if err != nil {
+			log.WithError(err).Error("Failed to get user info")
+			return result, err
+		}
+
+		addr := fmt.Sprintf("127.0.0.1:%v", bridge.GetIMAPPort())
+
+		for account, mboxMap := range state {
+			if progressCB != nil {
+				progressCB(fmt.Sprintf("Checking state for user %v's account '%v'", usr.Name(), account))
+			}
+			if err := func(account string, mboxMap user.AccountMailboxMap) error {
+				client, err := goimapclient.Dial(addr)
+				if err != nil {
+					log.WithError(err).Error("Failed to connect to imap client")
+					return err
+				}
+
+				defer func() {
+					_ = client.Logout()
+				}()
+
+				if err := client.Login(account, string(info.BridgePass)); err != nil {
+					return fmt.Errorf("failed to login for user %v:%w", usr.Name(), err)
+				}
+
+				log := log.WithField("account", account)
+				for mboxName, messageList := range mboxMap {
+					log := log.WithField("mbox", mboxName)
+					status, err := client.Select(mboxName, true)
+					if err != nil {
+						log.WithError(err).Errorf("Failed to select mailbox %v", messageList)
+						return fmt.Errorf("failed to select '%v':%w", mboxName, err)
+					}
+
+					log.Debug("Checking message count")
+
+					if int(status.Messages) != len(messageList) {
+						success = false
+						log.Errorf("Message count doesn't match, got '%v' expected '%v'", status.Messages, len(messageList))
+					}
+
+					ids, err := clientGetMessageIDs(client, mboxName)
+					if err != nil {
+						return fmt.Errorf("failed to get message ids for mbox '%v': %w", mboxName, err)
+					}
+
+					for _, msg := range messageList {
+						imapFlags, ok := ids[msg.ID]
+						if !ok {
+							if meta.FailedMessageIDs.Contains(msg.ID) {
+								log.Warningf("Missing message '%v', but it is part of failed message set", msg.ID)
+							} else {
+								log.Errorf("Missing message '%v'", msg.ID)
+							}
+
+							result.AddMissingMessage(msg.UserID, msg)
+							continue
+						}
+
+						if checkFlags {
+							if !imapFlags.Equals(msg.Flags) {
+								log.Errorf("Message '%v' flags do mot match, got=%v, expected=%v",
+									msg.ID,
+									imapFlags.ToSlice(),
+									msg.Flags.ToSlice(),
+								)
+							}
+						}
+					}
+				}
+
+				if !success {
+					log.Errorf("State does not match")
+				} else {
+					log.Info("State matches")
+				}
+
+				return nil
+			}(account, mboxMap); err != nil {
+				return result, err
+			}
+		}
+
+		// Check for orphaned messages (only present in All Mail)
+		if progressCB != nil {
+			progressCB(fmt.Sprintf("Checking user %v for orphans", usr.Name()))
+		}
+		log.Debugf("Checking for orphans")
+
+		for _, m := range meta.Metadata {
+			filteredLabels := xslices.Filter(m.LabelIDs, func(t string) bool {
+				switch t {
+				case proton.AllMailLabel:
+					return false
+				case proton.AllSentLabel:
+					return false
+				case proton.AllDraftsLabel:
+					return false
+				case proton.OutboxLabel:
+					return false
+				default:
+					return true
+				}
+			})
+
+			if len(filteredLabels) == 0 {
+				log.Warnf("Message %v is only present in All Mail (Subject=%v)", m.ID, m.Subject)
+			}
+		}
+	}
+
+	return result, nil
+}
+
+func (bridge *Bridge) DebugDownloadFailedMessages(
+	ctx context.Context,
+	result CheckClientStateResult,
+	exportPath string,
+	progressCB func(string, int, int),
+) error {
+	bridge.usersLock.RLock()
+	defer bridge.usersLock.RUnlock()
+
+	for userID, messages := range result.MissingMessages {
+		usr, ok := bridge.users[userID]
+		if !ok {
+			return fmt.Errorf("failed to find user with id %v", userID)
+		}
+
+		userDir := filepath.Join(exportPath, userID)
+		if err := os.MkdirAll(userDir, 0o700); err != nil {
+			return fmt.Errorf("failed to create directory '%v': %w", userDir, err)
+		}
+
+		if err := usr.DebugDownloadMessages(ctx, userDir, messages, progressCB); err != nil {
+			return err
+		}
+	}
+
+	return nil
+}
+
+func clientGetMessageIDs(client *goimapclient.Client, mailbox string) (map[string]imap.FlagSet, error) {
+	status, err := client.Select(mailbox, true)
+	if err != nil {
+		return nil, err
+	}
+
+	if status.Messages == 0 {
+		return nil, nil
+	}
+
+	resCh := make(chan *goimap.Message)
+
+	section, err := goimap.ParseBodySectionName("BODY[HEADER]")
+	if err != nil {
+		return nil, err
+	}
+
+	fetchItems := []goimap.FetchItem{"BODY[HEADER]", goimap.FetchFlags}
+
+	seq, err := goimap.ParseSeqSet("1:*")
+	if err != nil {
+		return nil, err
+	}
+
+	go func() {
+		if err := client.Fetch(
+			seq,
+			fetchItems,
+			resCh,
+		); err != nil {
+			panic(err)
+		}
+	}()
+
+	messages := iterator.Collect(iterator.Chan(resCh))
+
+	ids := make(map[string]imap.FlagSet, len(messages))
+
+	for i, m := range messages {
+		literal, err := io.ReadAll(m.GetBody(section))
+		if err != nil {
+			return nil, err
+		}
+
+		header, err := rfc822.NewHeader(literal)
+		if err != nil {
+			return nil, fmt.Errorf("failed to parse header for msg %v: %w", i, err)
+		}
+
+		internalID, ok := header.GetChecked("X-Pm-Internal-Id")
+		if !ok {
+			logrus.WithField("pkg", "bridge/debug").Errorf("Message %v does not have internal id", internalID)
+			continue
+		}
+
+		messageFlags := imap.NewFlagSet(m.Flags...)
+
+		// Recent and Deleted are not part of the proton flag set.
+		messageFlags.RemoveFromSelf("\\Recent")
+		messageFlags.RemoveFromSelf("\\Deleted")
+
+		ids[internalID] = messageFlags
+	}
+
+	return ids, nil
+}

internal/bridge/draft_test.go

@@ -0,0 +1,171 @@
+// Copyright (c) 2025 Proton AG
+//
+// This file is part of Proton Mail Bridge.
+//
+// Proton Mail Bridge is free software: you can redistribute it and/or modify
+// it under the terms of the GNU General Public License as published by
+// the Free Software Foundation, either version 3 of the License, or
+// (at your option) any later version.
+//
+// Proton Mail Bridge is distributed in the hope that it will be useful,
+// but WITHOUT ANY WARRANTY; without even the implied warranty of
+// MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+// GNU General Public License for more details.
+//
+// You should have received a copy of the GNU General Public License
+// along with Proton Mail Bridge.  If not, see <https://www.gnu.org/licenses/>.
+
+package bridge_test
+
+import (
+	"bytes"
+	"context"
+	"crypto/tls"
+	"fmt"
+	"io"
+	"net"
+	"strings"
+	"testing"
+	"time"
+
+	"github.com/ProtonMail/gluon/rfc822"
+	"github.com/ProtonMail/go-proton-api"
+	"github.com/ProtonMail/go-proton-api/server"
+	"github.com/ProtonMail/proton-bridge/v3/internal/bridge"
+	"github.com/ProtonMail/proton-bridge/v3/internal/constants"
+	"github.com/ProtonMail/proton-bridge/v3/internal/events"
+	go_imap "github.com/emersion/go-imap"
+	"github.com/emersion/go-sasl"
+	"github.com/emersion/go-smtp"
+	"github.com/sirupsen/logrus"
+	"github.com/stretchr/testify/require"
+)
+
+func TestBridge_HandleDraftsSendFromOtherClient(t *testing.T) {
+	getGluonHeaderID := func(literal []byte) (string, string) {
+		h, err := rfc822.NewHeader(literal)
+		require.NoError(t, err)
+
+		gluonID, ok := h.GetChecked("X-Pm-Gluon-Id")
+		require.True(t, ok)
+
+		externalID, ok := h.GetChecked("Message-Id")
+		require.True(t, ok)
+
+		return gluonID, externalID
+	}
+
+	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, storeKey []byte) {
+		_, _, err := s.CreateUser("imap", password)
+		require.NoError(t, err)
+
+		_, _, err = s.CreateUser("bar", password)
+		require.NoError(t, err)
+
+		// The initial user should be fully synced.
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(b *bridge.Bridge, _ *bridge.Mocks) {
+			syncCh, done := chToType[events.Event, events.SyncFinished](b.GetEvents(events.SyncFinished{}))
+			defer done()
+
+			userID, err := b.LoginFull(ctx, "imap", password, nil, nil)
+			require.NoError(t, err)
+
+			require.Equal(t, userID, (<-syncCh).UserID)
+
+			info, err := b.GetUserInfo(userID)
+			require.NoError(t, err)
+			require.True(t, info.State == bridge.Connected)
+
+			client, err := eventuallyDial(fmt.Sprintf("%v:%v", constants.Host, b.GetIMAPPort()))
+			require.NoError(t, err)
+			require.NoError(t, client.Login(info.Addresses[0], string(info.BridgePass)))
+			defer func() { _ = client.Logout() }()
+
+			// Create first draft in client.
+			literal := fmt.Sprintf(`From: %v
+To: %v
+Date: Fri, 3 Feb 2023 01:04:32 +0100
+Subject: Foo
+
+Hello
+`, info.Addresses[0], "bar@proton.local")
+
+			require.NoError(t, client.Append("Drafts", nil, time.Now(), strings.NewReader(literal)))
+			// Verify the draft is available in client.
+			require.Eventually(t, func() bool {
+				status, err := client.Status("Drafts", []go_imap.StatusItem{go_imap.StatusMessages})
+				require.NoError(t, err)
+				return status.Messages == 1
+			}, 2*time.Second, time.Second)
+
+			// Retrieve the new literal so we can have the Proton Message ID.
+			messages, err := clientFetch(client, "Drafts")
+			require.NoError(t, err)
+			require.Equal(t, 1, len(messages))
+
+			newLiteral, err := io.ReadAll(messages[0].GetBody(must(go_imap.ParseBodySectionName("BODY[]"))))
+			require.NoError(t, err)
+			logrus.Info(string(newLiteral))
+
+			newLiteralID, newLiteralExternID := getGluonHeaderID(newLiteral)
+
+			// Modify new literal.
+			newLiteralModified := append(newLiteral, []byte(" world from client2")...) //nolint:gocritic
+
+			func() {
+				smtpClient, err := smtp.Dial(net.JoinHostPort(constants.Host, fmt.Sprint(b.GetSMTPPort())))
+				require.NoError(t, err)
+				defer func() { _ = smtpClient.Close() }()
+
+				// Upgrade to TLS.
+				require.NoError(t, smtpClient.StartTLS(&tls.Config{InsecureSkipVerify: true}))
+
+				// Authorize with SASL PLAIN.
+				require.NoError(t, smtpClient.Auth(sasl.NewPlainClient(
+					info.Addresses[0],
+					info.Addresses[0],
+					string(info.BridgePass)),
+				))
+
+				// Send the message.
+				require.NoError(t, smtpClient.SendMail(
+					info.Addresses[0],
+					[]string{"bar@proton.local"},
+					bytes.NewReader(newLiteralModified),
+				))
+			}()
+
+			// Append message to Sent as the imap client would.
+			require.NoError(t, client.Append("Sent", nil, time.Now(), strings.NewReader(literal)))
+
+			// Verify the sent message gets updated with the new literal.
+			require.Eventually(t, func() bool {
+				// Check if sent message matches the latest draft.
+				messagesClient1, err := clientFetch(client, "Sent", "BODY[TEXT]", "BODY[]")
+				require.NoError(t, err)
+
+				if len(messagesClient1) != 1 {
+					return false
+				}
+
+				sentLiteral, err := io.ReadAll(messagesClient1[0].GetBody(must(go_imap.ParseBodySectionName("BODY[]"))))
+				require.NoError(t, err)
+
+				sentLiteralID, sentLiteralExternID := getGluonHeaderID(sentLiteral)
+
+				sentLiteralText, err := io.ReadAll(messagesClient1[0].GetBody(must(go_imap.ParseBodySectionName("BODY[TEXT]"))))
+				require.NoError(t, err)
+
+				sentLiteralStr := string(sentLiteralText)
+
+				literalMatches := sentLiteralStr == "Hello\r\n world from client2\r\n"
+
+				idIsDifferent := sentLiteralID != newLiteralID
+
+				externIDMatches := sentLiteralExternID == newLiteralExternID
+
+				return literalMatches && idIsDifferent && externIDMatches
+			}, 2*time.Second, time.Second)
+		})
+	}, server.WithMessageDedup())
+}

internal/bridge/errors.go

@@ -1,4 +1,4 @@
-// Copyright (c) 2023 Proton AG
+// Copyright (c) 2025 Proton AG
 //
 // This file is part of Proton Mail Bridge.
 //
@@ -22,9 +22,6 @@ import "errors"
 var (
 	ErrVaultInsecure = errors.New("the vault is insecure")
 	ErrVaultCorrupt  = errors.New("the vault is corrupt")
-
-	ErrServeIMAP    = errors.New("failed to serve IMAP")
-	ErrServeSMTP    = errors.New("failed to serve SMTP")
 	ErrWatchUpdates  = errors.New("failed to watch for updates")
 
 	ErrNoSuchUser          = errors.New("no such user")

internal/bridge/events.go

@@ -0,0 +1,45 @@
+// Copyright (c) 2025 Proton AG
+//
+// This file is part of Proton Mail Bridge.
+//
+// Proton Mail Bridge is free software: you can redistribute it and/or modify
+// it under the terms of the GNU General Public License as published by
+// the Free Software Foundation, either version 3 of the License, or
+// (at your option) any later version.
+//
+// Proton Mail Bridge is distributed in the hope that it will be useful,
+// but WITHOUT ANY WARRANTY; without even the implied warranty of
+// MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+// GNU General Public License for more details.
+//
+// You should have received a copy of the GNU General Public License
+// along with Proton Mail Bridge.  If not, see <https://www.gnu.org/licenses/>.
+
+package bridge
+
+import (
+	"context"
+
+	"github.com/ProtonMail/gluon/watcher"
+	"github.com/ProtonMail/proton-bridge/v3/internal/events"
+)
+
+type bridgeEventSubscription struct {
+	b *Bridge
+}
+
+func (b bridgeEventSubscription) Add(ofType ...events.Event) *watcher.Watcher[events.Event] {
+	return b.b.addWatcher(ofType...)
+}
+
+func (b bridgeEventSubscription) Remove(watcher *watcher.Watcher[events.Event]) {
+	b.b.remWatcher(watcher)
+}
+
+type bridgeEventPublisher struct {
+	b *Bridge
+}
+
+func (b bridgeEventPublisher) PublishEvent(_ context.Context, event events.Event) {
+	b.b.publish(event)
+}

internal/bridge/heartbeat.go

@@ -0,0 +1,167 @@
+// Copyright (c) 2025 Proton AG
+//
+// This file is part of Proton Mail Bridge.
+//
+// Proton Mail Bridge is free software: you can redistribute it and/or modify
+// it under the terms of the GNU General Public License as published by
+// the Free Software Foundation, either version 3 of the License, or
+// (at your option) any later version.
+//
+// Proton Mail Bridge is distributed in the hope that it will be useful,
+// but WITHOUT ANY WARRANTY; without even the implied warranty of
+// MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+// GNU General Public License for more details.
+//
+// You should have received a copy of the GNU General Public License
+// along with Proton Mail Bridge.  If not, see <https://www.gnu.org/licenses/>.
+
+package bridge
+
+import (
+	"context"
+	"encoding/json"
+	"sync"
+	"time"
+
+	"github.com/ProtonMail/gluon/async"
+	"github.com/ProtonMail/gluon/reporter"
+	"github.com/ProtonMail/proton-bridge/v3/internal/safe"
+	"github.com/ProtonMail/proton-bridge/v3/internal/telemetry"
+	"github.com/ProtonMail/proton-bridge/v3/internal/vault"
+	"github.com/sirupsen/logrus"
+)
+
+const HeartbeatCheckInterval = time.Hour
+
+type heartBeatState struct {
+	task *async.Group
+	telemetry.Heartbeat
+	taskLock     sync.Mutex
+	taskStarted  bool
+	taskInterval time.Duration
+}
+
+func newHeartBeatState(ctx context.Context, panicHandler async.PanicHandler) *heartBeatState {
+	return &heartBeatState{
+		task: async.NewGroup(ctx, panicHandler),
+	}
+}
+
+func (h *heartBeatState) init(bridge *Bridge, manager telemetry.HeartbeatManager) {
+	h.Heartbeat = telemetry.NewHeartbeat(manager, 1143, 1025, bridge.GetGluonCacheDir(), bridge.keychains.GetDefaultHelper())
+	h.taskInterval = manager.GetHeartbeatPeriodicInterval()
+	h.SetRollout(bridge.GetUpdateRollout())
+	h.SetAutoStart(bridge.GetAutostart())
+	h.SetAutoUpdate(bridge.GetAutoUpdate())
+	h.SetBeta(bridge.GetUpdateChannel())
+	h.SetDoh(bridge.GetProxyAllowed())
+	h.SetShowAllMail(bridge.GetShowAllMail())
+	h.SetIMAPConnectionMode(bridge.GetIMAPSSL())
+	h.SetSMTPConnectionMode(bridge.GetSMTPSSL())
+	h.SetIMAPPort(bridge.GetIMAPPort())
+	h.SetSMTPPort(bridge.GetSMTPPort())
+	h.SetCacheLocation(bridge.GetGluonCacheDir())
+	if val, err := bridge.GetKeychainApp(); err != nil {
+		h.SetKeyChainPref(val)
+	} else {
+		h.SetKeyChainPref(bridge.keychains.GetDefaultHelper())
+	}
+	h.SetPrevVersion(bridge.GetLastVersion().String())
+
+	safe.RLock(func() {
+		var splitMode = false
+		for _, user := range bridge.users {
+			if user.GetAddressMode() == vault.SplitMode {
+				splitMode = true
+			}
+			h.SetUserPlan(user.GetUserPlanName())
+		}
+		var numberConnectedAccounts = len(bridge.users)
+		h.SetNumberConnectedAccounts(numberConnectedAccounts)
+		h.SetSplitMode(splitMode)
+
+		// Do not try to send if there is no user yet.
+		if numberConnectedAccounts > 0 {
+			defer h.start()
+		}
+	}, bridge.usersLock)
+}
+
+func (h *heartBeatState) start() {
+	h.taskLock.Lock()
+	defer h.taskLock.Unlock()
+	if h.taskStarted {
+		return
+	}
+
+	h.taskStarted = true
+
+	h.task.PeriodicOrTrigger(h.taskInterval, 0, func(ctx context.Context) {
+		logrus.WithField("pkg", "bridge/heartbeat").Debug("Checking for heartbeat")
+
+		h.TrySending(ctx)
+	})
+}
+
+func (h *heartBeatState) stop() {
+	h.taskLock.Lock()
+	defer h.taskLock.Unlock()
+	if !h.taskStarted {
+		return
+	}
+
+	h.task.CancelAndWait()
+	h.taskStarted = false
+}
+
+func (bridge *Bridge) IsTelemetryAvailable(ctx context.Context) bool {
+	var flag = true
+	if bridge.GetTelemetryDisabled() {
+		return false
+	}
+
+	safe.RLock(func() {
+		for _, user := range bridge.users {
+			flag = flag && user.IsTelemetryEnabled(ctx)
+		}
+	}, bridge.usersLock)
+
+	return flag
+}
+
+func (bridge *Bridge) SendHeartbeat(ctx context.Context, heartbeat *telemetry.HeartbeatData) bool {
+	data, err := json.Marshal(heartbeat)
+	if err != nil {
+		if err := bridge.reporter.ReportMessageWithContext("Cannot parse heartbeat data.", reporter.Context{
+			"error": err,
+		}); err != nil {
+			logrus.WithField("pkg", "bridge/heartbeat").WithError(err).Error("Failed to parse heartbeat data.")
+		}
+		return false
+	}
+
+	var sent = false
+
+	safe.RLock(func() {
+		for _, user := range bridge.users {
+			if err := user.SendTelemetry(ctx, data); err == nil {
+				sent = true
+				break
+			}
+		}
+	}, bridge.usersLock)
+
+	return sent
+}
+
+func (bridge *Bridge) GetLastHeartbeatSent() time.Time {
+	return bridge.vault.GetLastHeartbeatSent()
+}
+
+func (bridge *Bridge) SetLastHeartbeatSent(timestamp time.Time) error {
+	return bridge.vault.SetLastHeartbeatSent(timestamp)
+}
+
+func (bridge *Bridge) GetHeartbeatPeriodicInterval() time.Duration {
+	return HeartbeatCheckInterval
+}

internal/bridge/identifier.go

@@ -1,4 +1,4 @@
-// Copyright (c) 2023 Proton AG
+// Copyright (c) 2025 Proton AG
 //
 // This file is part of Proton Mail Bridge.
 //
@@ -17,6 +17,10 @@
 
 package bridge
 
+import (
+	"github.com/sirupsen/logrus"
+)
+
 func (bridge *Bridge) GetCurrentUserAgent() string {
 	return bridge.identifier.GetUserAgent()
 }
@@ -24,3 +28,52 @@ func (bridge *Bridge) GetCurrentUserAgent() string {
 func (bridge *Bridge) SetCurrentPlatform(platform string) {
 	bridge.identifier.SetPlatform(platform)
 }
+
+func (bridge *Bridge) setUserAgent(name, version string) {
+	currentUserAgent := bridge.identifier.GetClientString()
+
+	bridge.heartbeat.SetContactedByAppleNotes(name)
+
+	bridge.identifier.SetClient(name, version)
+
+	newUserAgent := bridge.identifier.GetClientString()
+
+	if currentUserAgent != newUserAgent {
+		if err := bridge.vault.SetLastUserAgent(newUserAgent); err != nil {
+			logrus.WithError(err).Error("Failed to write new user agent to vault")
+		}
+	}
+}
+
+type bridgeUserAgentUpdater struct {
+	*Bridge
+}
+
+func (b *bridgeUserAgentUpdater) GetUserAgent() string {
+	return b.identifier.GetUserAgent()
+}
+
+func (b *bridgeUserAgentUpdater) HasClient() bool {
+	return b.identifier.HasClient()
+}
+
+func (b *bridgeUserAgentUpdater) SetClient(name, version string) {
+	b.heartbeat.SetContactedByAppleNotes(name)
+	b.identifier.SetClient(name, version)
+}
+
+func (b *bridgeUserAgentUpdater) SetPlatform(platform string) {
+	b.identifier.SetPlatform(platform)
+}
+
+func (b *bridgeUserAgentUpdater) SetClientString(client string) {
+	b.identifier.SetClientString(client)
+}
+
+func (b *bridgeUserAgentUpdater) GetClientString() string {
+	return b.identifier.GetClientString()
+}
+
+func (b *bridgeUserAgentUpdater) SetUserAgent(name, version string) {
+	b.setUserAgent(name, version)
+}

internal/bridge/imap.go

@@ -1,4 +1,4 @@
-// Copyright (c) 2023 Proton AG
+// Copyright (c) 2025 Proton AG
 //
 // This file is part of Proton Mail Bridge.
 //
@@ -20,338 +20,117 @@ package bridge
 import (
 	"context"
 	"crypto/tls"
-	"fmt"
-	"io"
-	"os"
-	"path/filepath"
+	"strings"
 
 	"github.com/Masterminds/semver/v3"
-	"github.com/ProtonMail/gluon"
 	imapEvents "github.com/ProtonMail/gluon/events"
-	"github.com/ProtonMail/gluon/reporter"
-	"github.com/ProtonMail/gluon/store"
-	"github.com/ProtonMail/proton-bridge/v3/internal/async"
-	"github.com/ProtonMail/proton-bridge/v3/internal/constants"
-	"github.com/ProtonMail/proton-bridge/v3/internal/logging"
-	"github.com/ProtonMail/proton-bridge/v3/internal/user"
-	"github.com/ProtonMail/proton-bridge/v3/internal/vault"
+	"github.com/ProtonMail/proton-bridge/v3/internal/events"
+	"github.com/ProtonMail/proton-bridge/v3/internal/services/imapsmtpserver"
+	"github.com/ProtonMail/proton-bridge/v3/internal/unleash"
+	"github.com/ProtonMail/proton-bridge/v3/internal/useragent"
 	"github.com/sirupsen/logrus"
 )
 
-const (
-	defaultClientName    = "UnknownClient"
-	defaultClientVersion = "0.0.1"
-)
-
-func (bridge *Bridge) serveIMAP() error {
-	if bridge.imapServer == nil {
-		return fmt.Errorf("no imap server instance running")
-	}
-
-	logrus.Info("Starting IMAP server")
-
-	imapListener, err := newListener(bridge.vault.GetIMAPPort(), bridge.vault.GetIMAPSSL(), bridge.tlsConfig)
-	if err != nil {
-		return fmt.Errorf("failed to create IMAP listener: %w", err)
-	}
-
-	bridge.imapListener = imapListener
-
-	if err := bridge.imapServer.Serve(context.Background(), bridge.imapListener); err != nil {
-		return fmt.Errorf("failed to serve IMAP: %w", err)
-	}
-
-	if err := bridge.vault.SetIMAPPort(getPort(imapListener.Addr())); err != nil {
-		return fmt.Errorf("failed to store IMAP port in vault: %w", err)
-	}
-
-	return nil
-}
-
-func (bridge *Bridge) restartIMAP() error {
-	logrus.Info("Restarting IMAP server")
-
-	if bridge.imapListener != nil {
-		if err := bridge.imapListener.Close(); err != nil {
-			return fmt.Errorf("failed to close IMAP listener: %w", err)
-		}
-	}
-
-	return bridge.serveIMAP()
-}
-
-func (bridge *Bridge) closeIMAP(ctx context.Context) error {
-	logrus.Info("Closing IMAP server")
-
-	if bridge.imapServer != nil {
-		if err := bridge.imapServer.Close(ctx); err != nil {
-			return fmt.Errorf("failed to close IMAP server: %w", err)
-		}
-		bridge.imapServer = nil
-	}
-
-	if bridge.imapListener != nil {
-		if err := bridge.imapListener.Close(); err != nil {
-			return fmt.Errorf("failed to close IMAP listener: %w", err)
-		}
-	}
-
-	return nil
-}
-
-// addIMAPUser connects the given user to gluon.
-//
-//nolint:funlen
-func (bridge *Bridge) addIMAPUser(ctx context.Context, user *user.User) error {
-	if bridge.imapServer == nil {
-		return fmt.Errorf("no imap server instance running")
-	}
-
-	imapConn, err := user.NewIMAPConnectors()
-	if err != nil {
-		return fmt.Errorf("failed to create IMAP connectors: %w", err)
-	}
-
-	for addrID, imapConn := range imapConn {
-		log := logrus.WithFields(logrus.Fields{
-			"userID": user.ID(),
-			"addrID": addrID,
-		})
-
-		if gluonID, ok := user.GetGluonID(addrID); ok {
-			log.WithField("gluonID", gluonID).Info("Loading existing IMAP user")
-
-			// Load the user, checking whether the DB was newly created.
-			isNew, err := bridge.imapServer.LoadUser(ctx, imapConn, gluonID, user.GluonKey())
-			if err != nil {
-				return fmt.Errorf("failed to load IMAP user: %w", err)
-			}
-
-			if isNew {
-				// If the DB was newly created, clear the sync status; gluon's DB was not found.
-				logrus.Warn("IMAP user DB was newly created, clearing sync status")
-
-				// Remove the user from IMAP so we can clear the sync status.
-				if err := bridge.imapServer.RemoveUser(ctx, gluonID, false); err != nil {
-					return fmt.Errorf("failed to remove IMAP user: %w", err)
-				}
-
-				// Clear the sync status -- we need to resync all messages.
-				if err := user.ClearSyncStatus(); err != nil {
-					return fmt.Errorf("failed to clear sync status: %w", err)
-				}
-
-				// Add the user back to the IMAP server.
-				if isNew, err := bridge.imapServer.LoadUser(ctx, imapConn, gluonID, user.GluonKey()); err != nil {
-					return fmt.Errorf("failed to add IMAP user: %w", err)
-				} else if isNew {
-					panic("IMAP user should already have a database")
-				}
-			} else if status := user.GetSyncStatus(); !status.HasLabels {
-				// Otherwise, the DB already exists -- if the labels are not yet synced, we need to re-create the DB.
-				if err := bridge.imapServer.RemoveUser(ctx, gluonID, true); err != nil {
-					return fmt.Errorf("failed to remove old IMAP user: %w", err)
-				}
-
-				if err := user.RemoveGluonID(addrID, gluonID); err != nil {
-					return fmt.Errorf("failed to remove old IMAP user ID: %w", err)
-				}
-
-				gluonID, err := bridge.imapServer.AddUser(ctx, imapConn, user.GluonKey())
-				if err != nil {
-					return fmt.Errorf("failed to add IMAP user: %w", err)
-				}
-
-				if err := user.SetGluonID(addrID, gluonID); err != nil {
-					return fmt.Errorf("failed to set IMAP user ID: %w", err)
-				}
-
-				log.WithField("gluonID", gluonID).Info("Re-created IMAP user")
-			}
-		} else {
-			log.Info("Creating new IMAP user")
-
-			gluonID, err := bridge.imapServer.AddUser(ctx, imapConn, user.GluonKey())
-			if err != nil {
-				return fmt.Errorf("failed to add IMAP user: %w", err)
-			}
-
-			if err := user.SetGluonID(addrID, gluonID); err != nil {
-				return fmt.Errorf("failed to set IMAP user ID: %w", err)
-			}
-
-			log.WithField("gluonID", gluonID).Info("Created new IMAP user")
-		}
-	}
-
-	// Trigger a sync for the user, if needed.
-	user.TriggerSync()
-
-	return nil
-}
-
-// removeIMAPUser disconnects the given user from gluon, optionally also removing its files.
-func (bridge *Bridge) removeIMAPUser(ctx context.Context, user *user.User, withData bool) error {
-	if bridge.imapServer == nil {
-		return fmt.Errorf("no imap server instance running")
-	}
-
-	logrus.WithFields(logrus.Fields{
-		"userID":   user.ID(),
-		"withData": withData,
-	}).Debug("Removing IMAP user")
-
-	for addrID, gluonID := range user.GetGluonIDs() {
-		if err := bridge.imapServer.RemoveUser(ctx, gluonID, withData); err != nil {
-			return fmt.Errorf("failed to remove IMAP user: %w", err)
-		}
-
-		if withData {
-			if err := user.RemoveGluonID(addrID, gluonID); err != nil {
-				return fmt.Errorf("failed to remove IMAP user ID: %w", err)
-			}
-		}
-	}
-
-	return nil
+func (bridge *Bridge) restartIMAP(ctx context.Context) error {
+	return bridge.serverManager.RestartIMAP(ctx)
 }
 
 func (bridge *Bridge) handleIMAPEvent(event imapEvents.Event) {
+	log := logrus.WithField("pkg", "bridge/event/imap")
+
 	switch event := event.(type) {
 	case imapEvents.UserAdded:
 		for labelID, count := range event.Counts {
-			logrus.WithFields(logrus.Fields{
+			log.WithFields(logrus.Fields{
 				"gluonID": event.UserID,
 				"labelID": labelID,
 				"count":   count,
 			}).Info("Received mailbox message count")
 		}
 
-	case imapEvents.SessionAdded:
-		if !bridge.identifier.HasClient() {
-			bridge.identifier.SetClient(defaultClientName, defaultClientVersion)
-		}
-
 	case imapEvents.IMAPID:
-		logrus.WithFields(logrus.Fields{
+		log.WithFields(logrus.Fields{
 			"sessionID": event.SessionID,
 			"name":      event.IMAPID.Name,
 			"version":   event.IMAPID.Version,
 		}).Info("Received IMAP ID")
 
 		if event.IMAPID.Name != "" && event.IMAPID.Version != "" {
-			bridge.identifier.SetClient(event.IMAPID.Name, event.IMAPID.Version)
+			bridge.setUserAgent(event.IMAPID.Name, event.IMAPID.Version)
+		}
+
+	case imapEvents.LoginFailed:
+		log.WithFields(logrus.Fields{
+			"sessionID": event.SessionID,
+			"username":  event.Username,
+			"pkg":       "imap",
+		}).Error("Incorrect login credentials.")
+		bridge.publish(events.IMAPLoginFailed{Username: event.Username})
+
+	case imapEvents.Login:
+		if strings.Contains(bridge.GetCurrentUserAgent(), useragent.DefaultUserAgent) {
+			bridge.setUserAgent(useragent.UnknownClient, useragent.DefaultVersion)
 		}
 	}
 }
 
-func getGluonDir(encVault *vault.Vault) (string, error) {
-	if err := os.MkdirAll(encVault.GetGluonCacheDir(), 0o700); err != nil {
-		return "", fmt.Errorf("failed to create gluon dir: %w", err)
+type bridgeIMAPSettings struct {
+	b *Bridge
+}
+
+func (b *bridgeIMAPSettings) EventPublisher() imapsmtpserver.IMAPEventPublisher {
+	return b
+}
+
+func (b *bridgeIMAPSettings) TLSConfig() *tls.Config {
+	return b.b.tlsConfig
+}
+
+func (b *bridgeIMAPSettings) LogClient() bool {
+	return b.b.logIMAPClient
+}
+
+func (b *bridgeIMAPSettings) LogServer() bool {
+	return b.b.logIMAPServer
+}
+
+func (b *bridgeIMAPSettings) DisableIMAPAuthenticate() bool {
+	return b.b.unleashService.GetFlagValue(unleash.IMAPAuthenticateCommandDisabled)
+}
+
+func (b *bridgeIMAPSettings) Port() int {
+	return b.b.vault.GetIMAPPort()
+}
+
+func (b *bridgeIMAPSettings) SetPort(i int) error {
+	return b.b.vault.SetIMAPPort(i)
+}
+
+func (b *bridgeIMAPSettings) UseSSL() bool {
+	return b.b.vault.GetIMAPSSL()
+}
+
+func (b *bridgeIMAPSettings) CacheDirectory() string {
+	return b.b.GetGluonCacheDir()
+}
+
+func (b *bridgeIMAPSettings) DataDirectory() (string, error) {
+	return b.b.GetGluonDataDir()
+}
+
+func (b *bridgeIMAPSettings) SetCacheDirectory(s string) error {
+	return b.b.vault.SetGluonDir(s)
+}
+
+func (b *bridgeIMAPSettings) Version() *semver.Version {
+	return b.b.curVersion
+}
+
+func (b *bridgeIMAPSettings) PublishIMAPEvent(ctx context.Context, event imapEvents.Event) {
+	select {
+	case <-ctx.Done():
+		return
+	case b.b.imapEventCh <- event:
+		// do nothing
 	}
-
-	return encVault.GetGluonCacheDir(), nil
-}
-
-func ApplyGluonCachePathSuffix(basePath string) string {
-	return filepath.Join(basePath, "backend", "store")
-}
-
-func ApplyGluonConfigPathSuffix(basePath string) string {
-	return filepath.Join(basePath, "backend", "db")
-}
-
-// nolint:funlen
-func newIMAPServer(
-	gluonCacheDir, gluonConfigDir string,
-	version *semver.Version,
-	tlsConfig *tls.Config,
-	reporter reporter.Reporter,
-	logClient, logServer bool,
-	eventCh chan<- imapEvents.Event,
-	tasks *async.Group,
-) (*gluon.Server, error) {
-	gluonCacheDir = ApplyGluonCachePathSuffix(gluonCacheDir)
-	gluonConfigDir = ApplyGluonConfigPathSuffix(gluonConfigDir)
-
-	logrus.WithFields(logrus.Fields{
-		"gluonStore": gluonCacheDir,
-		"gluonDB":    gluonConfigDir,
-		"version":    version,
-		"logClient":  logClient,
-		"logServer":  logServer,
-	}).Info("Creating IMAP server")
-
-	if logClient || logServer {
-		log := logrus.WithField("protocol", "IMAP")
-		log.Warning("================================================")
-		log.Warning("THIS LOG WILL CONTAIN **DECRYPTED** MESSAGE DATA")
-		log.Warning("================================================")
-	}
-
-	var imapClientLog io.Writer
-
-	if logClient {
-		imapClientLog = logging.NewIMAPLogger()
-	} else {
-		imapClientLog = io.Discard
-	}
-
-	var imapServerLog io.Writer
-
-	if logServer {
-		imapServerLog = logging.NewIMAPLogger()
-	} else {
-		imapServerLog = io.Discard
-	}
-
-	imapServer, err := gluon.New(
-		gluon.WithTLS(tlsConfig),
-		gluon.WithDataDir(gluonCacheDir),
-		gluon.WithDatabaseDir(gluonConfigDir),
-		gluon.WithStoreBuilder(new(storeBuilder)),
-		gluon.WithLogger(imapClientLog, imapServerLog),
-		getGluonVersionInfo(version),
-		gluon.WithReporter(reporter),
-	)
-	if err != nil {
-		return nil, err
-	}
-
-	tasks.Once(func(ctx context.Context) {
-		async.ForwardContext(ctx, eventCh, imapServer.AddWatcher())
-	})
-
-	tasks.Once(func(ctx context.Context) {
-		async.RangeContext(ctx, imapServer.GetErrorCh(), func(err error) {
-			logrus.WithError(err).Error("IMAP server error")
-		})
-	})
-
-	return imapServer, nil
-}
-
-func getGluonVersionInfo(version *semver.Version) gluon.Option {
-	return gluon.WithVersionInfo(
-		int(version.Major()),
-		int(version.Minor()),
-		int(version.Patch()),
-		constants.FullAppName,
-		"TODO",
-		"TODO",
-	)
-}
-
-type storeBuilder struct{}
-
-func (*storeBuilder) New(path, userID string, passphrase []byte) (store.Store, error) {
-	return store.NewOnDiskStore(
-		filepath.Join(path, userID),
-		passphrase,
-		store.WithCompressor(new(store.GZipCompressor)),
-	)
-}
-
-func (*storeBuilder) Delete(path, userID string) error {
-	return os.RemoveAll(filepath.Join(path, userID))
 }

internal/bridge/imapsmtp_telemetry.go

@@ -0,0 +1,26 @@
+// Copyright (c) 2025 Proton AG
+//
+// This file is part of Proton Mail Bridge.
+//
+// Proton Mail Bridge is free software: you can redistribute it and/or modify
+// it under the terms of the GNU General Public License as published by
+// the Free Software Foundation, either version 3 of the License, or
+// (at your option) any later version.
+//
+// Proton Mail Bridge is distributed in the hope that it will be useful,
+// but WITHOUT ANY WARRANTY; without even the implied warranty of
+// MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+// GNU General Public License for more details.
+//
+// You should have received a copy of the GNU General Public License
+// along with Proton Mail Bridge.  If not, see <https://www.gnu.org/licenses/>.
+
+package bridge
+
+type bridgeIMAPSMTPTelemetry struct {
+	b *Bridge
+}
+
+func (b bridgeIMAPSMTPTelemetry) SetCacheLocation(s string) {
+	b.b.heartbeat.SetCacheLocation(s)
+}

internal/bridge/keychain.go

@@ -0,0 +1,24 @@
+// Copyright (c) 2025 Proton AG
+//
+// This file is part of Proton Mail Bridge.
+//
+// Proton Mail Bridge is free software: you can redistribute it and/or modify
+// it under the terms of the GNU General Public License as published by
+// the Free Software Foundation, either version 3 of the License, or
+// (at your option) any later version.
+//
+// Proton Mail Bridge is distributed in the hope that it will be useful,
+// but WITHOUT ANY WARRANTY; without even the implied warranty of
+// MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+// GNU General Public License for more details.
+//
+// You should have received a copy of the GNU General Public License
+// along with Proton Mail Bridge.  If not, see <https://www.gnu.org/licenses/>.
+
+package bridge
+
+import "golang.org/x/exp/maps"
+
+func (bridge *Bridge) GetHelpersNames() []string {
+	return maps.Keys(bridge.keychains.GetHelpers())
+}

internal/bridge/locations.go

@@ -1,4 +1,4 @@
-// Copyright (c) 2023 Proton AG
+// Copyright (c) 2025 Proton AG
 //
 // This file is part of Proton Mail Bridge.
 //

internal/bridge/main_test.go

@@ -1,4 +1,4 @@
-// Copyright (c) 2023 Proton AG
+// Copyright (c) 2025 Proton AG
 //
 // This file is part of Proton Mail Bridge.
 //

internal/bridge/mocks.go

@@ -7,6 +7,7 @@ import (
 	"os"
 	"sync"
 	"testing"
+	"time"
 
 	"github.com/Masterminds/semver/v3"
 	"github.com/ProtonMail/proton-bridge/v3/internal/bridge/mocks"
@@ -24,6 +25,7 @@ type Mocks struct {
 
 	CrashHandler *mocks.MockPanicHandler
 	Reporter     *mocks.MockReporter
+	Heartbeat    *mocks.MockHeartbeatManager
 }
 
 func NewMocks(tb testing.TB, version, minAuto *semver.Version) *Mocks {
@@ -39,13 +41,18 @@ func NewMocks(tb testing.TB, version, minAuto *semver.Version) *Mocks {
 
 		CrashHandler: mocks.NewMockPanicHandler(ctl),
 		Reporter:     mocks.NewMockReporter(ctl),
+		Heartbeat:    mocks.NewMockHeartbeatManager(ctl),
 	}
 
 	// When getting the TLS issue channel, we want to return the test channel.
 	mocks.TLSReporter.EXPECT().GetTLSIssueCh().Return(mocks.TLSIssueCh).AnyTimes()
 
-	// This is called at he end of any go-routine:
-	mocks.CrashHandler.EXPECT().HandlePanic().AnyTimes()
+	// This is called at the end of any go-routine:
+	mocks.CrashHandler.EXPECT().HandlePanic(gomock.Any()).AnyTimes()
+
+	// this is called at start of heartbeat process.
+	mocks.Heartbeat.EXPECT().IsTelemetryAvailable(gomock.Any()).AnyTimes()
+	mocks.Heartbeat.EXPECT().GetHeartbeatPeriodicInterval().AnyTimes().Return(500 * time.Millisecond)
 
 	return mocks
 }
@@ -112,13 +119,14 @@ func (provider *TestLocationsProvider) UserCache() string {
 }
 
 type TestUpdater struct {
-	latest updater.VersionInfo
+	latest   updater.VersionInfoLegacy
+	releases updater.VersionInfo
 	lock     sync.RWMutex
 }
 
 func NewTestUpdater(version, minAuto *semver.Version) *TestUpdater {
 	return &TestUpdater{
-		latest: updater.VersionInfo{
+		latest: updater.VersionInfoLegacy{
 			Version: version,
 			MinAuto: minAuto,
 
@@ -127,11 +135,11 @@ func NewTestUpdater(version, minAuto *semver.Version) *TestUpdater {
 	}
 }
 
-func (testUpdater *TestUpdater) SetLatestVersion(version, minAuto *semver.Version) {
+func (testUpdater *TestUpdater) SetLatestVersionLegacy(version, minAuto *semver.Version) {
 	testUpdater.lock.Lock()
 	defer testUpdater.lock.Unlock()
 
-	testUpdater.latest = updater.VersionInfo{
+	testUpdater.latest = updater.VersionInfoLegacy{
 		Version: version,
 		MinAuto: minAuto,
 
@@ -139,13 +147,35 @@ func (testUpdater *TestUpdater) SetLatestVersion(version, minAuto *semver.Versio
 	}
 }
 
-func (testUpdater *TestUpdater) GetVersionInfo(ctx context.Context, downloader updater.Downloader, channel updater.Channel) (updater.VersionInfo, error) {
+func (testUpdater *TestUpdater) GetVersionInfoLegacy(_ context.Context, _ updater.Downloader, _ updater.Channel) (updater.VersionInfoLegacy, error) {
 	testUpdater.lock.RLock()
 	defer testUpdater.lock.RUnlock()
 
 	return testUpdater.latest, nil
 }
 
-func (testUpdater *TestUpdater) InstallUpdate(ctx context.Context, downloader updater.Downloader, update updater.VersionInfo) error {
+func (testUpdater *TestUpdater) InstallUpdateLegacy(_ context.Context, _ updater.Downloader, _ updater.VersionInfoLegacy) error {
+	return nil
+}
+
+func (testUpdater *TestUpdater) RemoveOldUpdates() error {
+	return nil
+}
+
+func (testUpdater *TestUpdater) SetLatestVersion(releases updater.VersionInfo) {
+	testUpdater.lock.Lock()
+	defer testUpdater.lock.Unlock()
+
+	testUpdater.releases = releases
+}
+
+func (testUpdater *TestUpdater) GetVersionInfo(_ context.Context, _ updater.Downloader) (updater.VersionInfo, error) {
+	testUpdater.lock.RLock()
+	defer testUpdater.lock.RUnlock()
+
+	return testUpdater.releases, nil
+}
+
+func (testUpdater *TestUpdater) InstallUpdate(_ context.Context, _ updater.Downloader, _ updater.Release) error {
 	return nil
 }

internal/bridge/mocks/async_mocks.go

@@ -1,5 +1,5 @@
 // Code generated by MockGen. DO NOT EDIT.
-// Source: github.com/ProtonMail/proton-bridge/v3/internal/async (interfaces: PanicHandler)
+// Source: github.com/ProtonMail/gluon/async (interfaces: PanicHandler)
 
 // Package mocks is a generated GoMock package.
 package mocks
@@ -34,13 +34,13 @@ func (m *MockPanicHandler) EXPECT() *MockPanicHandlerMockRecorder {
 }
 
 // HandlePanic mocks base method.
-func (m *MockPanicHandler) HandlePanic() {
+func (m *MockPanicHandler) HandlePanic(arg0 interface{}) {
 	m.ctrl.T.Helper()
-	m.ctrl.Call(m, "HandlePanic")
+	m.ctrl.Call(m, "HandlePanic", arg0)
 }
 
 // HandlePanic indicates an expected call of HandlePanic.
-func (mr *MockPanicHandlerMockRecorder) HandlePanic() *gomock.Call {
+func (mr *MockPanicHandlerMockRecorder) HandlePanic(arg0 interface{}) *gomock.Call {
 	mr.mock.ctrl.T.Helper()
-	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "HandlePanic", reflect.TypeOf((*MockPanicHandler)(nil).HandlePanic))
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "HandlePanic", reflect.TypeOf((*MockPanicHandler)(nil).HandlePanic), arg0)
 }

internal/bridge/mocks/matcher.go

@@ -1,4 +1,4 @@
-// Copyright (c) 2023 Proton AG
+// Copyright (c) 2025 Proton AG
 //
 // This file is part of Proton Mail Bridge.
 //

internal/bridge/mocks/observability_mocks.go

@@ -0,0 +1,49 @@
+package mocks
+
+import (
+	reflect "reflect"
+
+	"github.com/ProtonMail/go-proton-api"
+	"github.com/ProtonMail/proton-bridge/v3/internal/services/observability"
+	"github.com/golang/mock/gomock"
+)
+
+type MockObservabilitySender struct {
+	ctrl     *gomock.Controller
+	recorder *MockObservabilitySenderRecorder
+}
+
+type MockObservabilitySenderRecorder struct {
+	mock *MockObservabilitySender
+}
+
+func NewMockObservabilitySender(ctrl *gomock.Controller) *MockObservabilitySender {
+	mock := &MockObservabilitySender{ctrl: ctrl}
+	mock.recorder = &MockObservabilitySenderRecorder{mock: mock}
+	return mock
+}
+
+func (m *MockObservabilitySender) EXPECT() *MockObservabilitySenderRecorder { return m.recorder }
+
+func (m *MockObservabilitySender) AddDistinctMetrics(errType observability.DistinctionErrorTypeEnum, _ ...proton.ObservabilityMetric) {
+	m.ctrl.T.Helper()
+	m.ctrl.Call(m, "AddDistinctMetrics", errType)
+}
+
+func (m *MockObservabilitySender) AddMetrics(metrics ...proton.ObservabilityMetric) {
+	m.ctrl.T.Helper()
+	m.ctrl.Call(m, "AddMetrics", metrics)
+}
+
+func (mr *MockObservabilitySenderRecorder) AddDistinctMetrics(errType observability.DistinctionErrorTypeEnum, _ ...proton.ObservabilityMetric) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock,
+		"AddDistinctMetrics",
+		reflect.TypeOf((*MockObservabilitySender)(nil).AddDistinctMetrics),
+		errType)
+}
+
+func (mr *MockObservabilitySenderRecorder) AddMetrics(metrics ...proton.ObservabilityMetric) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "AddMetrics", reflect.TypeOf((*MockObservabilitySender)(nil).AddMetrics), metrics)
+}

internal/bridge/mocks/telemetry_mocks.go

@@ -0,0 +1,107 @@
+// Code generated by MockGen. DO NOT EDIT.
+// Source: github.com/ProtonMail/proton-bridge/v3/internal/telemetry (interfaces: HeartbeatManager)
+
+// Package mocks is a generated GoMock package.
+package mocks
+
+import (
+	context "context"
+	reflect "reflect"
+	time "time"
+
+	telemetry "github.com/ProtonMail/proton-bridge/v3/internal/telemetry"
+	gomock "github.com/golang/mock/gomock"
+)
+
+// MockHeartbeatManager is a mock of HeartbeatManager interface.
+type MockHeartbeatManager struct {
+	ctrl     *gomock.Controller
+	recorder *MockHeartbeatManagerMockRecorder
+}
+
+// MockHeartbeatManagerMockRecorder is the mock recorder for MockHeartbeatManager.
+type MockHeartbeatManagerMockRecorder struct {
+	mock *MockHeartbeatManager
+}
+
+// NewMockHeartbeatManager creates a new mock instance.
+func NewMockHeartbeatManager(ctrl *gomock.Controller) *MockHeartbeatManager {
+	mock := &MockHeartbeatManager{ctrl: ctrl}
+	mock.recorder = &MockHeartbeatManagerMockRecorder{mock}
+	return mock
+}
+
+// EXPECT returns an object that allows the caller to indicate expected use.
+func (m *MockHeartbeatManager) EXPECT() *MockHeartbeatManagerMockRecorder {
+	return m.recorder
+}
+
+// GetHeartbeatPeriodicInterval mocks base method.
+func (m *MockHeartbeatManager) GetHeartbeatPeriodicInterval() time.Duration {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "GetHeartbeatPeriodicInterval")
+	ret0, _ := ret[0].(time.Duration)
+	return ret0
+}
+
+// GetHeartbeatPeriodicInterval indicates an expected call of GetHeartbeatPeriodicInterval.
+func (mr *MockHeartbeatManagerMockRecorder) GetHeartbeatPeriodicInterval() *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "GetHeartbeatPeriodicInterval", reflect.TypeOf((*MockHeartbeatManager)(nil).GetHeartbeatPeriodicInterval))
+}
+
+// GetLastHeartbeatSent mocks base method.
+func (m *MockHeartbeatManager) GetLastHeartbeatSent() time.Time {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "GetLastHeartbeatSent")
+	ret0, _ := ret[0].(time.Time)
+	return ret0
+}
+
+// GetLastHeartbeatSent indicates an expected call of GetLastHeartbeatSent.
+func (mr *MockHeartbeatManagerMockRecorder) GetLastHeartbeatSent() *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "GetLastHeartbeatSent", reflect.TypeOf((*MockHeartbeatManager)(nil).GetLastHeartbeatSent))
+}
+
+// IsTelemetryAvailable mocks base method.
+func (m *MockHeartbeatManager) IsTelemetryAvailable(arg0 context.Context) bool {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "IsTelemetryAvailable", arg0)
+	ret0, _ := ret[0].(bool)
+	return ret0
+}
+
+// IsTelemetryAvailable indicates an expected call of IsTelemetryAvailable.
+func (mr *MockHeartbeatManagerMockRecorder) IsTelemetryAvailable(arg0 interface{}) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "IsTelemetryAvailable", reflect.TypeOf((*MockHeartbeatManager)(nil).IsTelemetryAvailable), arg0)
+}
+
+// SendHeartbeat mocks base method.
+func (m *MockHeartbeatManager) SendHeartbeat(arg0 context.Context, arg1 *telemetry.HeartbeatData) bool {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "SendHeartbeat", arg0, arg1)
+	ret0, _ := ret[0].(bool)
+	return ret0
+}
+
+// SendHeartbeat indicates an expected call of SendHeartbeat.
+func (mr *MockHeartbeatManagerMockRecorder) SendHeartbeat(arg0, arg1 interface{}) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "SendHeartbeat", reflect.TypeOf((*MockHeartbeatManager)(nil).SendHeartbeat), arg0, arg1)
+}
+
+// SetLastHeartbeatSent mocks base method.
+func (m *MockHeartbeatManager) SetLastHeartbeatSent(arg0 time.Time) error {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "SetLastHeartbeatSent", arg0)
+	ret0, _ := ret[0].(error)
+	return ret0
+}
+
+// SetLastHeartbeatSent indicates an expected call of SetLastHeartbeatSent.
+func (mr *MockHeartbeatManagerMockRecorder) SetLastHeartbeatSent(arg0 interface{}) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "SetLastHeartbeatSent", reflect.TypeOf((*MockHeartbeatManager)(nil).SetLastHeartbeatSent), arg0)
+}

internal/bridge/observability_test.go

@@ -0,0 +1,164 @@
+// Copyright (c) 2025 Proton AG
+//
+// This file is part of Proton Mail Bridge.
+//
+// Proton Mail Bridge is free software: you can redistribute it and/or modify
+// it under the terms of the GNU General Public License as published by
+// the Free Software Foundation, either version 3 of the License, or
+// (at your option) any later version.
+//
+// Proton Mail Bridge is distributed in the hope that it will be useful,
+// but WITHOUT ANY WARRANTY; without even the implied warranty of
+// MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+// GNU General Public License for more details.
+//
+// You should have received a copy of the GNU General Public License
+// along with Proton Mail Bridge.  If not, see <https://www.gnu.org/licenses/>.
+
+package bridge_test
+
+import (
+	"testing"
+	"time"
+
+	"github.com/ProtonMail/go-proton-api"
+	"github.com/ProtonMail/go-proton-api/server"
+	"github.com/ProtonMail/proton-bridge/v3/internal/bridge"
+	"github.com/ProtonMail/proton-bridge/v3/internal/services/observability"
+	"github.com/stretchr/testify/require"
+	"golang.org/x/net/context"
+)
+
+func TestBridge_Observability(t *testing.T) {
+	testMetric := proton.ObservabilityMetric{
+		Name:      "test1",
+		Version:   1,
+		Timestamp: time.Now().Unix(),
+		Data:      nil,
+	}
+
+	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, vaultKey []byte) {
+		throttlePeriod := time.Millisecond * 500
+		observability.ModifyThrottlePeriod(throttlePeriod)
+
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, vaultKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
+			require.NoError(t, getErr(bridge.LoginFull(ctx, username, password, nil, nil)))
+
+			bridge.PushObservabilityMetric(testMetric)
+			time.Sleep(time.Millisecond * 50) // Wait for the metric to be sent
+			require.Equal(t, 1, len(s.GetObservabilityStatistics().Metrics))
+
+			for i := 0; i < 10; i++ {
+				time.Sleep(time.Millisecond * 5) // Minor delay between each so our tests aren't flaky
+				bridge.PushObservabilityMetric(testMetric)
+			}
+			// We should still have only 1 metric sent as the throttleDuration has not passed
+			require.Equal(t, 1, len(s.GetObservabilityStatistics().Metrics))
+
+			// Wait for throttle duration to pass; we should have our remaining metrics posted
+			time.Sleep(throttlePeriod)
+			require.Equal(t, 11, len(s.GetObservabilityStatistics().Metrics))
+
+			// Wait for the throttle duration to reset; i.e. so we have enough time to send a request immediately
+			time.Sleep(throttlePeriod)
+			for i := 0; i < 10; i++ {
+				time.Sleep(time.Millisecond * 5)
+				bridge.PushObservabilityMetric(testMetric)
+			}
+			// We should only have one additional metric sent immediately
+			require.Equal(t, 12, len(s.GetObservabilityStatistics().Metrics))
+
+			// Wait for the others to be sent
+			time.Sleep(throttlePeriod)
+			require.Equal(t, 21, len(s.GetObservabilityStatistics().Metrics))
+
+			// Spam the endpoint a bit
+			for i := 0; i < 300; i++ {
+				if i < 200 {
+					time.Sleep(time.Millisecond * 10)
+				}
+				bridge.PushObservabilityMetric(testMetric)
+			}
+
+			// Ensure we've sent all metrics
+			time.Sleep(throttlePeriod)
+
+			observabilityStats := s.GetObservabilityStatistics()
+			require.Equal(t, 321, len(observabilityStats.Metrics))
+
+			// Verify that each request had a throttleDuration time difference between each request
+			for i := 0; i < len(observabilityStats.RequestTime)-1; i++ {
+				tOne := observabilityStats.RequestTime[i]
+				tTwo := observabilityStats.RequestTime[i+1]
+				require.True(t, tTwo.Sub(tOne).Abs() > throttlePeriod)
+			}
+		})
+	})
+}
+
+func TestBridge_Observability_Heartbeat(t *testing.T) {
+	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, vaultKey []byte) {
+		throttlePeriod := time.Millisecond * 300
+		observability.ModifyThrottlePeriod(throttlePeriod)
+
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, vaultKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
+			require.NoError(t, getErr(bridge.LoginFull(ctx, username, password, nil, nil)))
+			bridge.ModifyObservabilityHeartbeatInterval(throttlePeriod)
+
+			require.Equal(t, 0, len(s.GetObservabilityStatistics().Metrics))
+			time.Sleep(time.Millisecond * 150)
+			require.Equal(t, 0, len(s.GetObservabilityStatistics().Metrics))
+			time.Sleep(time.Millisecond * 200)
+			require.Equal(t, 1, len(s.GetObservabilityStatistics().Metrics))
+			time.Sleep(time.Millisecond * 350)
+			require.Equal(t, 2, len(s.GetObservabilityStatistics().Metrics))
+			time.Sleep(time.Millisecond * 350)
+			require.Equal(t, 3, len(s.GetObservabilityStatistics().Metrics))
+		})
+	})
+}
+
+func TestBridge_Observability_UserMetric(t *testing.T) {
+	testMetric := proton.ObservabilityMetric{
+		Name:      "test1",
+		Version:   1,
+		Timestamp: time.Now().Unix(),
+		Data:      nil,
+	}
+
+	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, vaultKey []byte) {
+		userMetricPeriod := time.Millisecond * 200
+		heartbeatPeriod := time.Second * 10
+		throttlePeriod := time.Millisecond * 100
+		observability.ModifyUserMetricInterval(userMetricPeriod)
+		observability.ModifyThrottlePeriod(throttlePeriod)
+
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, vaultKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
+			require.NoError(t, getErr(bridge.LoginFull(ctx, username, password, nil, nil)))
+			bridge.ModifyObservabilityHeartbeatInterval(heartbeatPeriod)
+
+			time.Sleep(throttlePeriod)
+			require.Equal(t, 0, len(s.GetObservabilityStatistics().Metrics))
+
+			bridge.PushDistinctObservabilityMetrics(observability.SyncError, testMetric)
+			time.Sleep(throttlePeriod)
+			// We're expecting two observability metrics to be sent, the actual metric + the user metric.
+			require.Equal(t, 2, len(s.GetObservabilityStatistics().Metrics))
+
+			bridge.PushDistinctObservabilityMetrics(observability.SyncError, testMetric)
+			time.Sleep(throttlePeriod)
+			// We're expecting only a single metric to be sent, since the user metric update has been sent already within the predefined period.
+			require.Equal(t, 3, len(s.GetObservabilityStatistics().Metrics))
+
+			bridge.PushDistinctObservabilityMetrics(observability.SyncError, testMetric)
+			time.Sleep(throttlePeriod)
+			// Two metric updates should be sent again.
+			require.Equal(t, 5, len(s.GetObservabilityStatistics().Metrics))
+
+			bridge.PushDistinctObservabilityMetrics(observability.SyncError, testMetric)
+			time.Sleep(throttlePeriod)
+			// Only a single one should be sent.
+			require.Equal(t, 6, len(s.GetObservabilityStatistics().Metrics))
+		})
+	})
+}

internal/bridge/refresh_test.go

@@ -1,4 +1,4 @@
-// Copyright (c) 2023 Proton AG
+// Copyright (c) 2025 Proton AG
 //
 // This file is part of Proton Mail Bridge.
 //
@@ -28,7 +28,6 @@ import (
 	"github.com/ProtonMail/proton-bridge/v3/internal/constants"
 	"github.com/ProtonMail/proton-bridge/v3/internal/events"
 	"github.com/bradenaw/juniper/iterator"
-	"github.com/emersion/go-imap/client"
 	"github.com/golang/mock/gomock"
 	"github.com/stretchr/testify/require"
 )
@@ -57,6 +56,7 @@ func TestBridge_Refresh(t *testing.T) {
 			require.Equal(t, userID, (<-syncCh).UserID)
 		})
 
+		var uidValidities = make(map[string]uint32, len(names))
 		// If we then connect an IMAP client, it should see all the labels with UID validity of 1.
 		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(b *bridge.Bridge, mocks *bridge.Mocks) {
 			mocks.Reporter.EXPECT().ReportMessageWithContext(gomock.Any(), gomock.Any()).AnyTimes()
@@ -65,7 +65,7 @@ func TestBridge_Refresh(t *testing.T) {
 			require.NoError(t, err)
 			require.True(t, info.State == bridge.Connected)
 
-			client, err := client.Dial(fmt.Sprintf("%v:%v", constants.Host, b.GetIMAPPort()))
+			client, err := eventuallyDial(fmt.Sprintf("%v:%v", constants.Host, b.GetIMAPPort()))
 			require.NoError(t, err)
 			require.NoError(t, client.Login(info.Addresses[0], string(info.BridgePass)))
 			defer func() { _ = client.Logout() }()
@@ -73,7 +73,7 @@ func TestBridge_Refresh(t *testing.T) {
 			for _, name := range names {
 				status, err := client.Select("Folders/"+name, false)
 				require.NoError(t, err)
-				require.Equal(t, uint32(1000), status.UidValidity)
+				uidValidities[name] = status.UidValidity
 			}
 		})
 
@@ -84,6 +84,11 @@ func TestBridge_Refresh(t *testing.T) {
 		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(b *bridge.Bridge, mocks *bridge.Mocks) {
 			mocks.Reporter.EXPECT().ReportMessageWithContext(gomock.Any(), gomock.Any()).AnyTimes()
 
+			// Wait for refresh event first
+			refreshCh, refreshChDone := chToType[events.Event, events.UserRefreshed](b.GetEvents(events.UserRefreshed{}))
+			defer refreshChDone()
+			require.Equal(t, userID, (<-refreshCh).UserID)
+			// Then sync event
 			syncCh, done := chToType[events.Event, events.SyncFinished](b.GetEvents(events.SyncFinished{}))
 			defer done()
 
@@ -98,7 +103,7 @@ func TestBridge_Refresh(t *testing.T) {
 			require.NoError(t, err)
 			require.True(t, info.State == bridge.Connected)
 
-			client, err := client.Dial(fmt.Sprintf("%v:%v", constants.Host, b.GetIMAPPort()))
+			client, err := eventuallyDial(fmt.Sprintf("%v:%v", constants.Host, b.GetIMAPPort()))
 			require.NoError(t, err)
 			require.NoError(t, client.Login(info.Addresses[0], string(info.BridgePass)))
 			defer func() { _ = client.Logout() }()
@@ -106,7 +111,7 @@ func TestBridge_Refresh(t *testing.T) {
 			for _, name := range names {
 				status, err := client.Select("Folders/"+name, false)
 				require.NoError(t, err)
-				require.Equal(t, uint32(1001), status.UidValidity)
+				require.Greater(t, status.UidValidity, uidValidities[name])
 			}
 		})
 	})

internal/bridge/send_test.go

@@ -1,4 +1,4 @@
-// Copyright (c) 2023 Proton AG
+// Copyright (c) 2025 Proton AG
 //
 // This file is part of Proton Mail Bridge.
 //
@@ -33,8 +33,8 @@ import (
 	"github.com/ProtonMail/proton-bridge/v3/internal/bridge"
 	"github.com/ProtonMail/proton-bridge/v3/internal/constants"
 	"github.com/ProtonMail/proton-bridge/v3/internal/events"
+	smtpservice "github.com/ProtonMail/proton-bridge/v3/internal/services/smtp"
 	"github.com/emersion/go-imap"
-	"github.com/emersion/go-imap/client"
 	"github.com/emersion/go-sasl"
 	"github.com/emersion/go-smtp"
 	"github.com/stretchr/testify/require"
@@ -91,13 +91,13 @@ func TestBridge_Send(t *testing.T) {
 			}
 
 			// Connect the sender IMAP client.
-			senderIMAPClient, err := client.Dial(net.JoinHostPort(constants.Host, fmt.Sprint(bridge.GetIMAPPort())))
+			senderIMAPClient, err := eventuallyDial(net.JoinHostPort(constants.Host, fmt.Sprint(bridge.GetIMAPPort())))
 			require.NoError(t, err)
 			require.NoError(t, senderIMAPClient.Login(senderInfo.Addresses[0], string(senderInfo.BridgePass)))
 			defer senderIMAPClient.Logout() //nolint:errcheck
 
 			// Connect the recipient IMAP client.
-			recipientIMAPClient, err := client.Dial(net.JoinHostPort(constants.Host, fmt.Sprint(bridge.GetIMAPPort())))
+			recipientIMAPClient, err := eventuallyDial(net.JoinHostPort(constants.Host, fmt.Sprint(bridge.GetIMAPPort())))
 			require.NoError(t, err)
 			require.NoError(t, recipientIMAPClient.Login(recipientInfo.Addresses[0], string(recipientInfo.BridgePass)))
 			defer recipientIMAPClient.Logout() //nolint:errcheck
@@ -135,19 +135,19 @@ func TestBridge_SendDraftFlags(t *testing.T) {
 		})
 
 		// Start the bridge.
-		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
+		withBridgeWaitForServers(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
 			// Get the sender user info.
 			userInfo, err := bridge.QueryUserInfo(username)
 			require.NoError(t, err)
 
 			// Connect the sender IMAP client.
-			imapClient, err := client.Dial(net.JoinHostPort(constants.Host, fmt.Sprint(bridge.GetIMAPPort())))
+			imapClient, err := eventuallyDial(net.JoinHostPort(constants.Host, fmt.Sprint(bridge.GetIMAPPort())))
 			require.NoError(t, err)
 			require.NoError(t, imapClient.Login(userInfo.Addresses[0], string(userInfo.BridgePass)))
 			defer imapClient.Logout() //nolint:errcheck
 
 			// The message to send.
-			const message = `Subject: Test\r\n\r\nHello world!`
+			message := fmt.Sprintf("From: %v\r\nDate: 01 Jan 1980 00:00:00 +0000\r\nSubject: Test\r\n\r\nHello world!", userInfo.Addresses[0])
 
 			// Save a draft.
 			require.NoError(t, imapClient.Append("Drafts", []string{imap.DraftFlag}, time.Now(), strings.NewReader(message)))
@@ -245,13 +245,13 @@ func TestBridge_SendInvite(t *testing.T) {
 		})
 
 		// Start the bridge.
-		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
+		withBridgeWaitForServers(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
 			// Get the sender user info.
 			userInfo, err := bridge.QueryUserInfo(username)
 			require.NoError(t, err)
 
 			// Connect the sender IMAP client.
-			imapClient, err := client.Dial(net.JoinHostPort(constants.Host, fmt.Sprint(bridge.GetIMAPPort())))
+			imapClient, err := eventuallyDial(net.JoinHostPort(constants.Host, fmt.Sprint(bridge.GetIMAPPort())))
 			require.NoError(t, err)
 			require.NoError(t, imapClient.Login(userInfo.Addresses[0], string(userInfo.BridgePass)))
 			defer imapClient.Logout() //nolint:errcheck
@@ -330,3 +330,408 @@ func TestBridge_SendInvite(t *testing.T) {
 		})
 	})
 }
+
+func TestBridge_SendAddTextBodyPartIfNotExists(t *testing.T) {
+	// NOTE: Prior to GODT-2887, these tests had inline images, however after the implementation to support
+	// inline images new parts are injected to reference inline images without content-id set. The images
+	// in this test have been changed to regular attachments to keep the original checks in place.
+	const messageMultipartWithoutText = `Content-Type: multipart/mixed;
+  boundary="Apple-Mail=_E7AC06C7-4EB2-4453-8CBB-80F4412A7C84"
+Subject: A new message
+Date: Mon, 13 Mar 2023 16:06:16 +0100
+
+
+--Apple-Mail=_E7AC06C7-4EB2-4453-8CBB-80F4412A7C84
+Content-Disposition: attachment;
+  filename=Cat_August_2010-4.jpeg
+Content-Type: image/jpeg;
+  name="Cat_August_2010-4.jpeg"
+Content-Transfer-Encoding: base64
+
+SGVsbG8gd29ybGQ=
+
+--Apple-Mail=_E7AC06C7-4EB2-4453-8CBB-80F4412A7C84--
+	`
+
+	const messageMultipartWithText = `Content-Type: multipart/mixed;
+  boundary="Apple-Mail=_E7AC06C7-4EB2-4453-8CBB-80F4412A7C84"
+Subject: A new message Part2 
+Date: Mon, 13 Mar 2023 16:06:16 +0100
+
+--Apple-Mail=_E7AC06C7-4EB2-4453-8CBB-80F4412A7C84
+Content-Disposition: attachment;
+  filename=Cat_August_2010-4.jpeg
+Content-Type: image/jpeg;
+  name="Cat_August_2010-4.jpeg"
+Content-Transfer-Encoding: base64
+
+SGVsbG8gd29ybGQ=
+
+--Apple-Mail=_E7AC06C7-4EB2-4453-8CBB-80F4412A7C84
+Content-Type: text/html;charset=utf8
+Content-Transfer-Encoding: quoted-printable
+
+Hello world
+
+--Apple-Mail=_E7AC06C7-4EB2-4453-8CBB-80F4412A7C84--
+`
+
+	const messageWithTextOnly = `Content-Type: text/plain;charset=utf8
+Content-Transfer-Encoding: quoted-printable
+Subject: A new message Part3
+Date: Mon, 13 Mar 2023 16:06:16 +0100
+
+Hello world
+
+`
+
+	const messageMultipartWithoutTextWithTextAttachment = `Content-Type: multipart/mixed;
+  boundary="Apple-Mail=_E7AC06C7-4EB2-4453-8CBB-80F4412A7C84"
+Subject: A new message Part4
+Date: Mon, 13 Mar 2023 16:06:16 +0100
+
+--Apple-Mail=_E7AC06C7-4EB2-4453-8CBB-80F4412A7C84
+Content-Type: text/plain; charset=UTF-8; name="text.txt"
+Content-Disposition: attachment; filename="text.txt"
+Content-Transfer-Encoding: base64
+
+SGVsbG8gd29ybGQK
+
+--Apple-Mail=_E7AC06C7-4EB2-4453-8CBB-80F4412A7C84--
+`
+	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, storeKey []byte) {
+		_, _, err := s.CreateUser("recipient", password)
+		require.NoError(t, err)
+
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
+			senderUserID, err := bridge.LoginFull(ctx, username, password, nil, nil)
+			require.NoError(t, err)
+
+			recipientUserID, err := bridge.LoginFull(ctx, "recipient", password, nil, nil)
+			require.NoError(t, err)
+
+			senderInfo, err := bridge.GetUserInfo(senderUserID)
+			require.NoError(t, err)
+
+			recipientInfo, err := bridge.GetUserInfo(recipientUserID)
+			require.NoError(t, err)
+
+			messages := []string{
+				messageMultipartWithoutText,
+				messageMultipartWithText,
+				messageWithTextOnly,
+				messageMultipartWithoutTextWithTextAttachment,
+			}
+
+			for _, m := range messages {
+				// Dial the server.
+				client, err := smtp.Dial(net.JoinHostPort(constants.Host, fmt.Sprint(bridge.GetSMTPPort())))
+				require.NoError(t, err)
+				defer client.Close() //nolint:errcheck
+
+				// Upgrade to TLS.
+				require.NoError(t, client.StartTLS(&tls.Config{InsecureSkipVerify: true}))
+
+				// Authorize with SASL LOGIN.
+				require.NoError(t, client.Auth(sasl.NewLoginClient(
+					senderInfo.Addresses[0],
+					string(senderInfo.BridgePass)),
+				))
+
+				// Send the message.
+				require.NoError(t, client.SendMail(
+					senderInfo.Addresses[0],
+					[]string{recipientInfo.Addresses[0]},
+					strings.NewReader(m),
+				))
+			}
+
+			// Connect the sender IMAP client.
+			senderIMAPClient, err := eventuallyDial(net.JoinHostPort(constants.Host, fmt.Sprint(bridge.GetIMAPPort())))
+			require.NoError(t, err)
+			require.NoError(t, senderIMAPClient.Login(senderInfo.Addresses[0], string(senderInfo.BridgePass)))
+			defer senderIMAPClient.Logout() //nolint:errcheck
+
+			// Connect the recipient IMAP client.
+			recipientIMAPClient, err := eventuallyDial(net.JoinHostPort(constants.Host, fmt.Sprint(bridge.GetIMAPPort())))
+			require.NoError(t, err)
+			require.NoError(t, recipientIMAPClient.Login(recipientInfo.Addresses[0], string(recipientInfo.BridgePass)))
+			defer recipientIMAPClient.Logout() //nolint:errcheck
+
+			require.Eventually(t, func() bool {
+				messages, err := clientFetch(senderIMAPClient, `Sent`, imap.FetchBodyStructure)
+				require.NoError(t, err)
+				if len(messages) != 4 {
+					return false
+				}
+
+				// messages may not be in order
+				for _, message := range messages {
+					switch {
+					case message.Envelope.Subject == "A new message":
+						// The message that was sent should now include an empty text/plain body part since there was none
+						// in the original message.
+						require.Equal(t, 2, len(message.BodyStructure.Parts))
+
+						require.Equal(t, "text", message.BodyStructure.Parts[0].MIMEType)
+						require.Equal(t, "plain", message.BodyStructure.Parts[0].MIMESubType)
+						require.Equal(t, uint32(0), message.BodyStructure.Parts[0].Size)
+						require.Equal(t, "image", message.BodyStructure.Parts[1].MIMEType)
+						require.Equal(t, "jpeg", message.BodyStructure.Parts[1].MIMESubType)
+
+					case message.Envelope.Subject == "A new message Part2":
+						// This message already has a text body, should be unchanged
+						require.Equal(t, 2, len(message.BodyStructure.Parts))
+
+						require.Equal(t, "image", message.BodyStructure.Parts[1].MIMEType)
+						require.Equal(t, "jpeg", message.BodyStructure.Parts[1].MIMESubType)
+						require.Equal(t, "text", message.BodyStructure.Parts[0].MIMEType)
+						require.Equal(t, "html", message.BodyStructure.Parts[0].MIMESubType)
+
+					case message.Envelope.Subject == "A new message Part3":
+						// This message already has a text body, should be unchanged
+						require.Equal(t, 0, len(message.BodyStructure.Parts))
+
+						require.Equal(t, "text", message.BodyStructure.MIMEType)
+						require.Equal(t, "plain", message.BodyStructure.MIMESubType)
+
+					case message.Envelope.Subject == "A new message Part4":
+						// The message that was sent should now include an empty text/plain body part since even though
+						// there was only a text/plain attachment in the original message.
+						require.Equal(t, 2, len(message.BodyStructure.Parts))
+
+						require.Equal(t, "text", message.BodyStructure.Parts[0].MIMEType)
+						require.Equal(t, "plain", message.BodyStructure.Parts[0].MIMESubType)
+						require.Equal(t, uint32(0), message.BodyStructure.Parts[0].Size)
+						require.Equal(t, "text", message.BodyStructure.Parts[1].MIMEType)
+						require.Equal(t, "plain", message.BodyStructure.Parts[1].MIMESubType)
+						require.Equal(t, "attachment", message.BodyStructure.Parts[1].Disposition)
+					}
+				}
+
+				return true
+			}, 10*time.Second, 100*time.Millisecond)
+		})
+	})
+}
+
+func TestBridge_SendInlineImage(t *testing.T) {
+	const messageInlineImageOnly = `Content-Type: multipart/mixed;
+  boundary="Apple-Mail=_E7AC06C7-4EB2-4453-8CBB-80F4412A7C84"
+Subject: A new message
+Date: Mon, 13 Mar 2023 16:06:16 +0100
+
+
+--Apple-Mail=_E7AC06C7-4EB2-4453-8CBB-80F4412A7C84
+Content-Disposition: inline;
+  filename=Cat_August_2010-4.jpeg
+Content-Type: image/jpeg;
+  name="Cat_August_2010-4.jpeg"
+Content-Transfer-Encoding: base64
+
+SGVsbG8gd29ybGQ=
+
+--Apple-Mail=_E7AC06C7-4EB2-4453-8CBB-80F4412A7C84--
+	`
+
+	const messageInlineImageWithHTML = `Content-Type: multipart/mixed;
+  boundary="Apple-Mail=_E7AC06C7-4EB2-4453-8CBB-80F4412A7C84"
+Subject: A new message Part2 
+Date: Mon, 13 Mar 2023 16:06:16 +0100
+
+--Apple-Mail=_E7AC06C7-4EB2-4453-8CBB-80F4412A7C84
+Content-Type: text/html;charset=utf8
+Content-Transfer-Encoding: quoted-printable
+
+Hello world
+
+--Apple-Mail=_E7AC06C7-4EB2-4453-8CBB-80F4412A7C84
+Content-Disposition: inline;
+  filename=Cat_August_2010-4.jpeg
+Content-Type: image/jpeg;
+  name="Cat_August_2010-4.jpeg"
+Content-Transfer-Encoding: base64
+
+SGVsbG8gd29ybGQ=
+
+--Apple-Mail=_E7AC06C7-4EB2-4453-8CBB-80F4412A7C84--
+`
+
+	const messageInlineImageWithText = `Content-Type: multipart/mixed;
+  boundary="Apple-Mail=_E7AC06C7-4EB2-4453-8CBB-80F4412A7C84"
+Subject: A new message Part3
+Date: Mon, 13 Mar 2023 16:06:16 +0100
+
+--Apple-Mail=_E7AC06C7-4EB2-4453-8CBB-80F4412A7C84
+Content-Type: text/plain;charset=utf8
+Content-Transfer-Encoding: quoted-printable
+
+Hello world
+
+--Apple-Mail=_E7AC06C7-4EB2-4453-8CBB-80F4412A7C84
+Content-Disposition: inline;
+  filename=Cat_August_2010-4.jpeg
+Content-Type: image/jpeg;
+  name="Cat_August_2010-4.jpeg"
+Content-Transfer-Encoding: base64
+
+SGVsbG8gd29ybGQ=
+
+--Apple-Mail=_E7AC06C7-4EB2-4453-8CBB-80F4412A7C84--
+`
+
+	const messageInlineImageFollowedByText = `Content-Type: multipart/mixed;
+  boundary="Apple-Mail=_E7AC06C7-4EB2-4453-8CBB-80F4412A7C84"
+Subject: A new message Part4
+Date: Mon, 13 Mar 2023 16:06:16 +0100
+
+--Apple-Mail=_E7AC06C7-4EB2-4453-8CBB-80F4412A7C84
+Content-Disposition: inline;
+  filename=Cat_August_2010-4.jpeg
+Content-Type: image/jpeg;
+  name="Cat_August_2010-4.jpeg"
+Content-Transfer-Encoding: base64
+
+SGVsbG8gd29ybGQ=
+
+--Apple-Mail=_E7AC06C7-4EB2-4453-8CBB-80F4412A7C84
+Content-Type: text/plain;charset=utf8
+Content-Transfer-Encoding: quoted-printable
+
+Hello world
+
+--Apple-Mail=_E7AC06C7-4EB2-4453-8CBB-80F4412A7C84--
+`
+	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, storeKey []byte) {
+		_, _, err := s.CreateUser("recipient", password)
+		require.NoError(t, err)
+
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
+			senderUserID, err := bridge.LoginFull(ctx, username, password, nil, nil)
+			require.NoError(t, err)
+
+			recipientUserID, err := bridge.LoginFull(ctx, "recipient", password, nil, nil)
+			require.NoError(t, err)
+
+			senderInfo, err := bridge.GetUserInfo(senderUserID)
+			require.NoError(t, err)
+
+			recipientInfo, err := bridge.GetUserInfo(recipientUserID)
+			require.NoError(t, err)
+
+			messages := []string{
+				messageInlineImageOnly,
+				messageInlineImageWithHTML,
+				messageInlineImageWithText,
+				messageInlineImageFollowedByText,
+			}
+
+			for _, m := range messages {
+				// Dial the server.
+				client, err := smtp.Dial(net.JoinHostPort(constants.Host, fmt.Sprint(bridge.GetSMTPPort())))
+				require.NoError(t, err)
+				defer client.Close() //nolint:errcheck
+
+				// Upgrade to TLS.
+				require.NoError(t, client.StartTLS(&tls.Config{InsecureSkipVerify: true}))
+
+				// Authorize with SASL LOGIN.
+				require.NoError(t, client.Auth(sasl.NewLoginClient(
+					senderInfo.Addresses[0],
+					string(senderInfo.BridgePass)),
+				))
+
+				// Send the message.
+				require.NoError(t, client.SendMail(
+					senderInfo.Addresses[0],
+					[]string{recipientInfo.Addresses[0]},
+					strings.NewReader(m),
+				))
+			}
+
+			// Connect the sender IMAP client.
+			senderIMAPClient, err := eventuallyDial(net.JoinHostPort(constants.Host, fmt.Sprint(bridge.GetIMAPPort())))
+			require.NoError(t, err)
+			require.NoError(t, senderIMAPClient.Login(senderInfo.Addresses[0], string(senderInfo.BridgePass)))
+			defer senderIMAPClient.Logout() //nolint:errcheck
+
+			// Connect the recipient IMAP client.
+			recipientIMAPClient, err := eventuallyDial(net.JoinHostPort(constants.Host, fmt.Sprint(bridge.GetIMAPPort())))
+			require.NoError(t, err)
+			require.NoError(t, recipientIMAPClient.Login(recipientInfo.Addresses[0], string(recipientInfo.BridgePass)))
+			defer recipientIMAPClient.Logout() //nolint:errcheck
+
+			require.Eventually(t, func() bool {
+				messages, err := clientFetch(senderIMAPClient, `Sent`, imap.FetchBodyStructure)
+				require.NoError(t, err)
+				if len(messages) != 4 {
+					return false
+				}
+
+				// messages may not be in order
+				for _, message := range messages {
+					require.Equal(t, 1, len(message.BodyStructure.Parts))
+					require.Equal(t, "multipart", message.BodyStructure.MIMEType)
+					require.Equal(t, "mixed", message.BodyStructure.MIMESubType)
+					require.Equal(t, "multipart", message.BodyStructure.Parts[0].MIMEType)
+					require.Equal(t, "related", message.BodyStructure.Parts[0].MIMESubType)
+					require.Len(t, message.BodyStructure.Parts[0].Parts, 2)
+					require.Equal(t, "text", message.BodyStructure.Parts[0].Parts[0].MIMEType)
+					require.Equal(t, "html", message.BodyStructure.Parts[0].Parts[0].MIMESubType)
+					require.Equal(t, "image", message.BodyStructure.Parts[0].Parts[1].MIMEType)
+					require.Equal(t, "jpeg", message.BodyStructure.Parts[0].Parts[1].MIMESubType)
+				}
+
+				return true
+			}, 10*time.Second, 100*time.Millisecond)
+		})
+	})
+}
+
+func TestBridge_SendAddressDisabled(t *testing.T) {
+	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, storeKey []byte) {
+		recipientUserID, _, err := s.CreateUser("recipient", password)
+		require.NoError(t, err)
+
+		senderUserID, addrID, err := s.CreateUser("sender", password)
+		require.NoError(t, err)
+
+		require.NoError(t, s.ChangeAddressAllowSend(senderUserID, addrID, false))
+
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
+			senderUserID, err := bridge.LoginFull(ctx, "sender", password, nil, nil)
+			require.NoError(t, err)
+
+			_, err = bridge.LoginFull(ctx, "recipient", password, nil, nil)
+			require.NoError(t, err)
+
+			recipientInfo, err := bridge.GetUserInfo(recipientUserID)
+			require.NoError(t, err)
+
+			senderInfo, err := bridge.GetUserInfo(senderUserID)
+			require.NoError(t, err)
+
+			// Dial the server.
+			client, err := smtp.Dial(net.JoinHostPort(constants.Host, fmt.Sprint(bridge.GetSMTPPort())))
+			require.NoError(t, err)
+			defer client.Close() //nolint:errcheck
+
+			// Upgrade to TLS.
+			require.NoError(t, client.StartTLS(&tls.Config{InsecureSkipVerify: true}))
+			require.NoError(t, client.Auth(sasl.NewLoginClient(
+				senderInfo.Addresses[0],
+				string(senderInfo.BridgePass)),
+			))
+
+			// Send the message.
+			err = client.SendMail(
+				senderInfo.Addresses[0],
+				[]string{recipientInfo.Addresses[0]},
+				strings.NewReader("Subject: Test 1\r\n\r\nHello world!"),
+			)
+
+			smtpErr := smtpservice.NewErrCannotSendFromAddress(senderInfo.Addresses[0])
+			require.Equal(t, fmt.Sprintf("Error: %v", smtpErr.Error()), err.Error())
+		})
+	})
+}

internal/bridge/sentry_test.go

@@ -1,4 +1,4 @@
-// Copyright (c) 2023 Proton AG
+// Copyright (c) 2025 Proton AG
 //
 // This file is part of Proton Mail Bridge.
 //
@@ -29,13 +29,12 @@ import (
 	"github.com/ProtonMail/proton-bridge/v3/internal/bridge"
 	"github.com/ProtonMail/proton-bridge/v3/internal/constants"
 	"github.com/ProtonMail/proton-bridge/v3/internal/events"
-	"github.com/golang/mock/gomock"
 	"github.com/stretchr/testify/require"
 )
 
 func TestBridge_Report(t *testing.T) {
 	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, storeKey []byte) {
-		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(b *bridge.Bridge, mocks *bridge.Mocks) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(b *bridge.Bridge, _ *bridge.Mocks) {
 			syncCh, done := chToType[events.Event, events.SyncFinished](b.GetEvents(events.SyncFinished{}))
 			defer done()
 
@@ -56,12 +55,6 @@ func TestBridge_Report(t *testing.T) {
 			require.NoError(t, err)
 			defer func() { require.NoError(t, conn.Close()) }()
 
-			// Sending garbage to the IMAP port should cause the bridge to report it.
-			mocks.Reporter.EXPECT().ReportMessageWithContext(
-				gomock.Eq("Failed to parse IMAP command"),
-				gomock.Any(),
-			).Return(nil)
-
 			// Read lines from the IMAP port.
 			lineCh := liner.New(conn).Lines(func() error { return nil })
 

internal/bridge/server_manager_test.go

@@ -0,0 +1,137 @@
+// Copyright (c) 2025 Proton AG
+//
+// This file is part of Proton Mail Bridge.
+//
+// Proton Mail Bridge is free software: you can redistribute it and/or modify
+// it under the terms of the GNU General Public License as published by
+// the Free Software Foundation, either version 3 of the License, or
+// (at your option) any later version.
+//
+// Proton Mail Bridge is distributed in the hope that it will be useful,
+// but WITHOUT ANY WARRANTY; without even the implied warranty of
+// MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+// GNU General Public License for more details.
+//
+// You should have received a copy of the GNU General Public License
+// along with Proton Mail Bridge.  If not, see <https://www.gnu.org/licenses/>.
+
+package bridge_test
+
+import (
+	"context"
+	"fmt"
+	"net"
+	"testing"
+
+	"github.com/ProtonMail/go-proton-api"
+	"github.com/ProtonMail/go-proton-api/server"
+	"github.com/ProtonMail/proton-bridge/v3/internal/bridge"
+	"github.com/ProtonMail/proton-bridge/v3/internal/constants"
+	"github.com/ProtonMail/proton-bridge/v3/internal/events"
+	"github.com/emersion/go-smtp"
+	"github.com/stretchr/testify/require"
+)
+
+func TestServerManager_ServersStartWithBridge(t *testing.T) {
+	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, storeKey []byte) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
+			imapClient, err := eventuallyDial(fmt.Sprintf("%v:%v", constants.Host, bridge.GetIMAPPort()))
+			require.NoError(t, err)
+			require.NoError(t, imapClient.Logout())
+
+			smtpClient, err := smtp.Dial(net.JoinHostPort(constants.Host, fmt.Sprint(bridge.GetSMTPPort())))
+			require.NoError(t, err)
+			smtpClient.Close() //nolint:errcheck
+		})
+	})
+}
+
+func TestServerManager_ServersKeepsRunningfterUserLogsOut(t *testing.T) {
+	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, storeKey []byte) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
+			userID, err := bridge.LoginFull(ctx, username, password, nil, nil)
+			require.NoError(t, err)
+
+			require.NoError(t, bridge.LogoutUser(ctx, userID))
+
+			imapClient, err := eventuallyDial(fmt.Sprintf("%v:%v", constants.Host, bridge.GetIMAPPort()))
+			require.NoError(t, err)
+			require.NoError(t, imapClient.Logout())
+
+			smtpClient, err := smtp.Dial(net.JoinHostPort(constants.Host, fmt.Sprint(bridge.GetSMTPPort())))
+			require.NoError(t, err)
+			smtpClient.Close() //nolint:errcheck
+		})
+	})
+}
+
+func TestServerManager_ServersDoNotStopWhenThereIsStillOneActiveUser(t *testing.T) {
+	otherPassword := []byte("bar")
+	otherUser := "foo"
+	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, storeKey []byte) {
+		_, _, err := s.CreateUser(otherUser, otherPassword)
+		require.NoError(t, err)
+
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
+			_, err := bridge.LoginFull(ctx, username, password, nil, nil)
+			require.NoError(t, err)
+
+			userIDOther, err := bridge.LoginFull(ctx, otherUser, otherPassword, nil, nil)
+			require.NoError(t, err)
+
+			evtCh, cancel := bridge.GetEvents(events.UserDeauth{})
+			defer cancel()
+
+			require.NoError(t, s.RevokeUser(userIDOther))
+
+			waitForEvent(t, evtCh, events.UserDeauth{})
+
+			imapClient, err := eventuallyDial(fmt.Sprintf("%v:%v", constants.Host, bridge.GetIMAPPort()))
+			require.NoError(t, err)
+			require.NoError(t, imapClient.Logout())
+
+			smtpClient, err := smtp.Dial(net.JoinHostPort(constants.Host, fmt.Sprint(bridge.GetSMTPPort())))
+			require.NoError(t, err)
+			smtpClient.Close() //nolint:errcheck
+		})
+	})
+}
+
+func TestServerManager_NetworkLossStopsServers(t *testing.T) {
+	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, storeKey []byte) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
+			imapWaiter := waitForIMAPServerReady(bridge)
+			defer imapWaiter.Done()
+
+			smtpWaiter := waitForSMTPServerReady(bridge)
+			defer smtpWaiter.Done()
+
+			imapWaiterStop := waitForIMAPServerStopped(bridge)
+			defer imapWaiterStop.Done()
+
+			smtpWaiterStop := waitForSMTPServerStopped(bridge)
+			defer smtpWaiterStop.Done()
+
+			_, err := bridge.LoginFull(ctx, username, password, nil, nil)
+			require.NoError(t, err)
+
+			imapClient, err := eventuallyDial(fmt.Sprintf("%v:%v", constants.Host, bridge.GetIMAPPort()))
+			require.NoError(t, err)
+			require.NoError(t, imapClient.Logout())
+
+			smtpClient, err := smtp.Dial(net.JoinHostPort(constants.Host, fmt.Sprint(bridge.GetSMTPPort())))
+			require.NoError(t, err)
+			smtpClient.Close() //nolint:errcheck
+
+			netCtl.Disable()
+
+			imapWaiterStop.Wait()
+			smtpWaiterStop.Wait()
+
+			netCtl.Enable()
+
+			imapWaiter.Wait()
+			smtpWaiter.Wait()
+		})
+	})
+}

internal/bridge/settings.go

@@ -1,4 +1,4 @@
-// Copyright (c) 2023 Proton AG
+// Copyright (c) 2025 Proton AG
 //
 // This file is part of Proton Mail Bridge.
 //
@@ -20,17 +20,13 @@ package bridge
 import (
 	"context"
 	"fmt"
-	"net"
-	"os"
-	"path/filepath"
 
 	"github.com/Masterminds/semver/v3"
-	"github.com/ProtonMail/proton-bridge/v3/internal/constants"
+	"github.com/ProtonMail/proton-bridge/v3/internal/kb"
 	"github.com/ProtonMail/proton-bridge/v3/internal/safe"
+	"github.com/ProtonMail/proton-bridge/v3/internal/services/userevents"
 	"github.com/ProtonMail/proton-bridge/v3/internal/updater"
 	"github.com/ProtonMail/proton-bridge/v3/internal/vault"
-	"github.com/ProtonMail/proton-bridge/v3/pkg/keychain"
-	"github.com/sirupsen/logrus"
 )
 
 func (bridge *Bridge) GetKeychainApp() (string, error) {
@@ -48,6 +44,8 @@ func (bridge *Bridge) SetKeychainApp(helper string) error {
 		return err
 	}
 
+	bridge.heartbeat.SetKeyChainPref(helper)
+
 	return vault.SetHelper(vaultDir, helper)
 }
 
@@ -55,7 +53,7 @@ func (bridge *Bridge) GetIMAPPort() int {
 	return bridge.vault.GetIMAPPort()
 }
 
-func (bridge *Bridge) SetIMAPPort(newPort int) error {
+func (bridge *Bridge) SetIMAPPort(ctx context.Context, newPort int) error {
 	if newPort == bridge.vault.GetIMAPPort() {
 		return nil
 	}
@@ -64,14 +62,16 @@ func (bridge *Bridge) SetIMAPPort(newPort int) error {
 		return err
 	}
 
-	return bridge.restartIMAP()
+	bridge.heartbeat.SetIMAPPort(newPort)
+
+	return bridge.restartIMAP(ctx)
 }
 
 func (bridge *Bridge) GetIMAPSSL() bool {
 	return bridge.vault.GetIMAPSSL()
 }
 
-func (bridge *Bridge) SetIMAPSSL(newSSL bool) error {
+func (bridge *Bridge) SetIMAPSSL(ctx context.Context, newSSL bool) error {
 	if newSSL == bridge.vault.GetIMAPSSL() {
 		return nil
 	}
@@ -80,14 +80,16 @@ func (bridge *Bridge) SetIMAPSSL(newSSL bool) error {
 		return err
 	}
 
-	return bridge.restartIMAP()
+	bridge.heartbeat.SetIMAPConnectionMode(newSSL)
+
+	return bridge.restartIMAP(ctx)
 }
 
 func (bridge *Bridge) GetSMTPPort() int {
 	return bridge.vault.GetSMTPPort()
 }
 
-func (bridge *Bridge) SetSMTPPort(newPort int) error {
+func (bridge *Bridge) SetSMTPPort(ctx context.Context, newPort int) error {
 	if newPort == bridge.vault.GetSMTPPort() {
 		return nil
 	}
@@ -96,14 +98,16 @@ func (bridge *Bridge) SetSMTPPort(newPort int) error {
 		return err
 	}
 
-	return bridge.restartSMTP()
+	bridge.heartbeat.SetSMTPPort(newPort)
+
+	return bridge.restartSMTP(ctx)
 }
 
 func (bridge *Bridge) GetSMTPSSL() bool {
 	return bridge.vault.GetSMTPSSL()
 }
 
-func (bridge *Bridge) SetSMTPSSL(newSSL bool) error {
+func (bridge *Bridge) SetSMTPSSL(ctx context.Context, newSSL bool) error {
 	if newSSL == bridge.vault.GetSMTPSSL() {
 		return nil
 	}
@@ -112,7 +116,9 @@ func (bridge *Bridge) SetSMTPSSL(newSSL bool) error {
 		return err
 	}
 
-	return bridge.restartSMTP()
+	bridge.heartbeat.SetSMTPConnectionMode(newSSL)
+
+	return bridge.restartSMTP(ctx)
 }
 
 func (bridge *Bridge) GetGluonCacheDir() string {
@@ -124,99 +130,39 @@ func (bridge *Bridge) GetGluonDataDir() (string, error) {
 }
 
 func (bridge *Bridge) SetGluonDir(ctx context.Context, newGluonDir string) error {
-	return safe.RLockRet(func() error {
-		currentGluonDir := bridge.GetGluonCacheDir()
-		newGluonDir = filepath.Join(newGluonDir, "gluon")
-		if newGluonDir == currentGluonDir {
-			return fmt.Errorf("new gluon dir is the same as the old one")
+	bridge.usersLock.RLock()
+
+	defer func() {
+		logPkg.Info("Restarting user event loops")
+		for _, u := range bridge.users {
+			u.ResumeEventLoop()
 		}
 
-		if err := bridge.stopEventLoops(); err != nil {
-			return err
-		}
-		defer func() {
-			err := bridge.startEventLoops(ctx)
-			if err != nil {
-				panic(err)
-			}
+		bridge.usersLock.RUnlock()
 	}()
 
-		if err := bridge.moveGluonCacheDir(currentGluonDir, newGluonDir); err != nil {
-			logrus.WithError(err).Error("failed to move GluonCacheDir")
-			if err := bridge.vault.SetGluonDir(currentGluonDir); err != nil {
-				panic(err)
+	type waiter struct {
+		w  *userevents.EventPollWaiter
+		id string
+	}
+
+	waiters := make([]waiter, 0, len(bridge.users))
+
+	logPkg.Info("Pausing user event loops for gluon dir change")
+	for id, u := range bridge.users {
+		waiters = append(waiters, waiter{w: u.PauseEventLoopWithWaiter(), id: id})
+	}
+
+	logPkg.Info("Waiting on user event loop completion")
+	for _, waiter := range waiters {
+		if err := waiter.w.WaitPollFinished(ctx); err != nil {
+			logPkg.WithError(err).Errorf("Failed to wait on event loop pause for user %v", waiter.id)
+			return fmt.Errorf("failed on event loop pause: %w", err)
 		}
 	}
 
-		gluonDataDir, err := bridge.GetGluonDataDir()
-		if err != nil {
-			panic(fmt.Errorf("failed to get Gluon Database directory: %w", err))
-		}
-
-		imapServer, err := newIMAPServer(
-			bridge.vault.GetGluonCacheDir(),
-			gluonDataDir,
-			bridge.curVersion,
-			bridge.tlsConfig,
-			bridge.reporter,
-			bridge.logIMAPClient,
-			bridge.logIMAPServer,
-			bridge.imapEventCh,
-			bridge.tasks,
-		)
-		if err != nil {
-			panic(fmt.Errorf("failed to create new IMAP server: %w", err))
-		}
-
-		bridge.imapServer = imapServer
-
-		return nil
-	}, bridge.usersLock)
-}
-
-func (bridge *Bridge) moveGluonCacheDir(oldGluonDir, newGluonDir string) error {
-	logrus.Infof("gluon cache moving from %s to %s", oldGluonDir, newGluonDir)
-	oldCacheDir := ApplyGluonCachePathSuffix(oldGluonDir)
-	if err := copyDir(oldCacheDir, ApplyGluonCachePathSuffix(newGluonDir)); err != nil {
-		return fmt.Errorf("failed to copy gluon dir: %w", err)
-	}
-
-	if err := bridge.vault.SetGluonDir(newGluonDir); err != nil {
-		return fmt.Errorf("failed to set new gluon cache dir: %w", err)
-	}
-
-	if err := os.RemoveAll(oldCacheDir); err != nil {
-		logrus.WithError(err).Error("failed to remove old gluon cache dir")
-	}
-	return nil
-}
-
-func (bridge *Bridge) stopEventLoops() error {
-	if err := bridge.closeIMAP(context.Background()); err != nil {
-		return fmt.Errorf("failed to close IMAP: %w", err)
-	}
-
-	if err := bridge.closeSMTP(); err != nil {
-		return fmt.Errorf("failed to close SMTP: %w", err)
-	}
-	return nil
-}
-
-func (bridge *Bridge) startEventLoops(ctx context.Context) error {
-	for _, user := range bridge.users {
-		if err := bridge.addIMAPUser(ctx, user); err != nil {
-			return fmt.Errorf("failed to add users to new IMAP server: %w", err)
-		}
-	}
-
-	if err := bridge.serveIMAP(); err != nil {
-		panic(fmt.Errorf("failed to serve IMAP: %w", err))
-	}
-
-	if err := bridge.serveSMTP(); err != nil {
-		panic(fmt.Errorf("failed to serve SMTP: %w", err))
-	}
-	return nil
+	logPkg.Info("Changing gluon directory")
+	return bridge.serverManager.SetGluonDir(ctx, newGluonDir)
 }
 
 func (bridge *Bridge) GetProxyAllowed() bool {
@@ -230,6 +176,8 @@ func (bridge *Bridge) SetProxyAllowed(allowed bool) error {
 		bridge.proxyCtl.DisallowProxy()
 	}
 
+	bridge.heartbeat.SetDoh(allowed)
+
 	return bridge.vault.SetProxyAllowed(allowed)
 }
 
@@ -243,6 +191,8 @@ func (bridge *Bridge) SetShowAllMail(show bool) error {
 			user.SetShowAllMail(show)
 		}
 
+		bridge.heartbeat.SetShowAllMail(show)
+
 		return bridge.vault.SetShowAllMail(show)
 	}, bridge.usersLock)
 }
@@ -256,6 +206,8 @@ func (bridge *Bridge) SetAutostart(autostart bool) error {
 		if err := bridge.vault.SetAutostart(autostart); err != nil {
 			return err
 		}
+
+		bridge.heartbeat.SetAutoStart(autostart)
 	}
 
 	var err error
@@ -276,6 +228,10 @@ func (bridge *Bridge) SetAutostart(autostart bool) error {
 	return err
 }
 
+func (bridge *Bridge) GetUpdateRollout() float64 {
+	return bridge.vault.GetUpdateRollout()
+}
+
 func (bridge *Bridge) GetAutoUpdate() bool {
 	return bridge.vault.GetAutoUpdate()
 }
@@ -289,11 +245,31 @@ func (bridge *Bridge) SetAutoUpdate(autoUpdate bool) error {
 		return err
 	}
 
+	bridge.heartbeat.SetAutoUpdate(autoUpdate)
+
 	bridge.goUpdate()
 
 	return nil
 }
 
+func (bridge *Bridge) GetTelemetryDisabled() bool {
+	return bridge.vault.GetTelemetryDisabled()
+}
+
+func (bridge *Bridge) SetTelemetryDisabled(isDisabled bool) error {
+	if err := bridge.vault.SetTelemetryDisabled(isDisabled); err != nil {
+		return err
+	}
+	// If telemetry is re-enabled locally, try to send the heartbeat.
+	if isDisabled {
+		bridge.heartbeat.stop()
+	} else {
+		bridge.heartbeat.start()
+	}
+
+	return nil
+}
+
 func (bridge *Bridge) GetUpdateChannel() updater.Channel {
 	return bridge.vault.GetUpdateChannel()
 }
@@ -307,6 +283,8 @@ func (bridge *Bridge) SetUpdateChannel(channel updater.Channel) error {
 		return err
 	}
 
+	bridge.heartbeat.SetBeta(channel)
+
 	bridge.goUpdate()
 
 	return nil
@@ -332,6 +310,13 @@ func (bridge *Bridge) SetColorScheme(colorScheme string) error {
 	return bridge.vault.SetColorScheme(colorScheme)
 }
 
+func (bridge *Bridge) GetKnowledgeBaseSuggestions(userInput string) (kb.ArticleList, error) {
+	return kb.GetSuggestions(userInput)
+}
+
+// FactoryReset deletes all users, wipes the vault, and deletes all files.
+// Note: it does not clear the keychain. The only entry in the keychain is the vault password,
+// which we need at next startup to decrypt the vault.
 func (bridge *Bridge) FactoryReset(ctx context.Context) {
 	// Delete all the users.
 	safe.Lock(func() {
@@ -343,38 +328,13 @@ func (bridge *Bridge) FactoryReset(ctx context.Context) {
 	// Wipe the vault.
 	gluonCacheDir, err := bridge.locator.ProvideGluonCachePath()
 	if err != nil {
-		logrus.WithError(err).Error("Failed to provide gluon dir")
+		logPkg.WithError(err).Error("Failed to provide gluon dir")
 	} else if err := bridge.vault.Reset(gluonCacheDir); err != nil {
-		logrus.WithError(err).Error("Failed to reset vault")
+		logPkg.WithError(err).Error("Failed to reset vault")
 	}
 
-	// Then delete all files.
-	if err := bridge.locator.Clear(); err != nil {
-		logrus.WithError(err).Error("Failed to clear data paths")
-	}
-
-	// Lastly clear the keychain.
-	vaultDir, err := bridge.locator.ProvideSettingsPath()
-	if err != nil {
-		logrus.WithError(err).Error("Failed to get vault dir")
-	} else if helper, err := vault.GetHelper(vaultDir); err != nil {
-		logrus.WithError(err).Error("Failed to get keychain helper")
-	} else if keychain, err := keychain.NewKeychain(helper, constants.KeyChainName); err != nil {
-		logrus.WithError(err).Error("Failed to get keychain")
-	} else if err := keychain.Clear(); err != nil {
-		logrus.WithError(err).Error("Failed to clear keychain")
-	}
-}
-
-func getPort(addr net.Addr) int {
-	switch addr := addr.(type) {
-	case *net.TCPAddr:
-		return addr.Port
-
-	case *net.UDPAddr:
-		return addr.Port
-
-	default:
-		return 0
+	// Lastly, delete all files except the vault.
+	if err := bridge.locator.Clear(bridge.vault.Path()); err != nil {
+		logPkg.WithError(err).Error("Failed to clear data paths")
 	}
 }

internal/bridge/settings_test.go

@@ -1,4 +1,4 @@
-// Copyright (c) 2023 Proton AG
+// Copyright (c) 2025 Proton AG
 //
 // This file is part of Proton Mail Bridge.
 //
@@ -25,12 +25,13 @@ import (
 	"github.com/ProtonMail/go-proton-api"
 	"github.com/ProtonMail/go-proton-api/server"
 	"github.com/ProtonMail/proton-bridge/v3/internal/bridge"
+	"github.com/ProtonMail/proton-bridge/v3/internal/events"
 	"github.com/stretchr/testify/require"
 )
 
 func TestBridge_Settings_GluonDir(t *testing.T) {
 	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, storeKey []byte) {
-		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, mocks *bridge.Mocks) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
 			// Create a user.
 			_, err := bridge.LoginFull(context.Background(), username, password, nil, nil)
 			require.NoError(t, err)
@@ -51,13 +52,52 @@ func TestBridge_Settings_GluonDir(t *testing.T) {
 	})
 }
 
+func TestBridge_Settings_GluonDirWithOnGoingEvents(t *testing.T) {
+	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, storeKey []byte) {
+		userID, addrID, err := s.CreateUser("imap", password)
+		require.NoError(t, err)
+
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
+			syncCh, done := chToType[events.Event, events.SyncFinished](bridge.GetEvents(events.SyncFinished{}))
+			defer done()
+
+			_, err := bridge.LoginFull(context.Background(), "imap", password, nil, nil)
+			require.NoError(t, err)
+
+			<-syncCh
+		})
+
+		labelID, err := s.CreateLabel(userID, "folder", "", proton.LabelTypeFolder)
+		require.NoError(t, err)
+
+		withClient(ctx, t, s, "imap", password, func(ctx context.Context, c *proton.Client) {
+			createNumMessages(ctx, t, c, addrID, labelID, 200)
+		})
+
+		withBridgeWaitForServers(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
+			// Create a new location for the Gluon data.
+			newGluonDir := t.TempDir()
+
+			// Move the gluon dir; it should also move the user's data.
+			require.NoError(t, bridge.SetGluonDir(context.Background(), newGluonDir))
+
+			// Check that the new directory is not empty.
+			entries, err := os.ReadDir(newGluonDir)
+			require.NoError(t, err)
+
+			// There should be at least one entry.
+			require.NotEmpty(t, entries)
+		})
+	})
+}
+
 func TestBridge_Settings_IMAPPort(t *testing.T) {
 	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, storeKey []byte) {
-		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, mocks *bridge.Mocks) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
 			curPort := bridge.GetIMAPPort()
 
 			// Set the port to 1144.
-			require.NoError(t, bridge.SetIMAPPort(1144))
+			require.NoError(t, bridge.SetIMAPPort(ctx, 1144))
 
 			// Get the new setting.
 			require.Equal(t, 1144, bridge.GetIMAPPort())
@@ -70,12 +110,12 @@ func TestBridge_Settings_IMAPPort(t *testing.T) {
 
 func TestBridge_Settings_IMAPSSL(t *testing.T) {
 	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, storeKey []byte) {
-		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, mocks *bridge.Mocks) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
 			// By default, IMAP SSL is disabled.
 			require.False(t, bridge.GetIMAPSSL())
 
 			// Enable IMAP SSL.
-			require.NoError(t, bridge.SetIMAPSSL(true))
+			require.NoError(t, bridge.SetIMAPSSL(ctx, true))
 
 			// Get the new setting.
 			require.True(t, bridge.GetIMAPSSL())
@@ -85,11 +125,11 @@ func TestBridge_Settings_IMAPSSL(t *testing.T) {
 
 func TestBridge_Settings_SMTPPort(t *testing.T) {
 	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, storeKey []byte) {
-		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, mocks *bridge.Mocks) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
 			curPort := bridge.GetSMTPPort()
 
 			// Set the port to 1024.
-			require.NoError(t, bridge.SetSMTPPort(1024))
+			require.NoError(t, bridge.SetSMTPPort(ctx, 1024))
 
 			// Get the new setting.
 			require.Equal(t, 1024, bridge.GetSMTPPort())
@@ -102,12 +142,12 @@ func TestBridge_Settings_SMTPPort(t *testing.T) {
 
 func TestBridge_Settings_SMTPSSL(t *testing.T) {
 	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, storeKey []byte) {
-		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, mocks *bridge.Mocks) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
 			// By default, SMTP SSL is disabled.
 			require.False(t, bridge.GetSMTPSSL())
 
 			// Enable SMTP SSL.
-			require.NoError(t, bridge.SetSMTPSSL(true))
+			require.NoError(t, bridge.SetSMTPSSL(ctx, true))
 
 			// Get the new setting.
 			require.True(t, bridge.GetSMTPSSL())
@@ -158,7 +198,7 @@ func TestBridge_Settings_Autostart(t *testing.T) {
 
 func TestBridge_Settings_FirstStart(t *testing.T) {
 	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, storeKey []byte) {
-		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, mocks *bridge.Mocks) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
 			// By default, first start is true.
 			require.True(t, bridge.GetFirstStart())
 

internal/bridge/smtp.go

@@ -1,4 +1,4 @@
-// Copyright (c) 2023 Proton AG
+// Copyright (c) 2025 Proton AG
 //
 // This file is part of Proton Mail Bridge.
 //
@@ -20,97 +20,38 @@ package bridge
 import (
 	"context"
 	"crypto/tls"
-	"fmt"
 
-	"github.com/ProtonMail/proton-bridge/v3/internal/logging"
-
-	"github.com/ProtonMail/proton-bridge/v3/internal/constants"
-	"github.com/emersion/go-sasl"
-	"github.com/emersion/go-smtp"
-	"github.com/sirupsen/logrus"
+	"github.com/ProtonMail/proton-bridge/v3/internal/identifier"
 )
 
-func (bridge *Bridge) serveSMTP() error {
-	logrus.Info("Starting SMTP server")
-
-	smtpListener, err := newListener(bridge.vault.GetSMTPPort(), bridge.vault.GetSMTPSSL(), bridge.tlsConfig)
-	if err != nil {
-		return fmt.Errorf("failed to create SMTP listener: %w", err)
-	}
-
-	bridge.smtpListener = smtpListener
-
-	bridge.tasks.Once(func(context.Context) {
-		if err := bridge.smtpServer.Serve(smtpListener); err != nil {
-			logrus.WithError(err).Info("SMTP server stopped")
-		}
-	})
-
-	if err := bridge.vault.SetSMTPPort(getPort(smtpListener.Addr())); err != nil {
-		return fmt.Errorf("failed to store SMTP port in vault: %w", err)
-	}
-
-	return nil
+func (bridge *Bridge) restartSMTP(ctx context.Context) error {
+	return bridge.serverManager.RestartSMTP(ctx)
 }
 
-func (bridge *Bridge) restartSMTP() error {
-	logrus.Info("Restarting SMTP server")
-
-	if err := bridge.closeSMTP(); err != nil {
-		return fmt.Errorf("failed to close SMTP: %w", err)
-	}
-
-	bridge.smtpServer = newSMTPServer(bridge, bridge.tlsConfig, bridge.logSMTP)
-
-	return bridge.serveSMTP()
+type bridgeSMTPSettings struct {
+	b *Bridge
 }
 
-// We close the listener ourselves even though it's also closed by smtpServer.Close().
-// This is because smtpServer.Serve() is called in a separate goroutine and might be executed
-// after we've already closed the server. However, go-smtp has a bug; it blocks on the listener
-// even after the server has been closed. So we close the listener ourselves to unblock it.
-func (bridge *Bridge) closeSMTP() error {
-	logrus.Info("Closing SMTP server")
-
-	if bridge.smtpListener != nil {
-		if err := bridge.smtpListener.Close(); err != nil {
-			return fmt.Errorf("failed to close SMTP listener: %w", err)
-		}
-	}
-
-	if err := bridge.smtpServer.Close(); err != nil {
-		logrus.WithError(err).Debug("Failed to close SMTP server (expected -- we close the listener ourselves)")
-	}
-
-	return nil
+func (b *bridgeSMTPSettings) TLSConfig() *tls.Config {
+	return b.b.tlsConfig
 }
 
-func newSMTPServer(bridge *Bridge, tlsConfig *tls.Config, logSMTP bool) *smtp.Server {
-	logrus.WithField("logSMTP", logSMTP).Info("Creating SMTP server")
-
-	smtpServer := smtp.NewServer(&smtpBackend{Bridge: bridge})
-
-	smtpServer.TLSConfig = tlsConfig
-	smtpServer.Domain = constants.Host
-	smtpServer.AllowInsecureAuth = true
-	smtpServer.MaxLineLength = 1 << 16
-	smtpServer.ErrorLog = logging.NewSMTPLogger()
-
-	// go-smtp suppors SASL PLAIN but not LOGIN. We need to add LOGIN support ourselves.
-	smtpServer.EnableAuth(sasl.Login, func(conn *smtp.Conn) sasl.Server {
-		return sasl.NewLoginServer(func(username, password string) error {
-			return conn.Session().AuthPlain(username, password)
-		})
-	})
-
-	if logSMTP {
-		log := logrus.WithField("protocol", "SMTP")
-		log.Warning("================================================")
-		log.Warning("THIS LOG WILL CONTAIN **DECRYPTED** MESSAGE DATA")
-		log.Warning("================================================")
-
-		smtpServer.Debug = logging.NewSMTPDebugLogger()
-	}
-
-	return smtpServer
+func (b *bridgeSMTPSettings) Log() bool {
+	return b.b.logSMTP
+}
+
+func (b *bridgeSMTPSettings) Port() int {
+	return b.b.vault.GetSMTPPort()
+}
+
+func (b *bridgeSMTPSettings) SetPort(i int) error {
+	return b.b.vault.SetSMTPPort(i)
+}
+
+func (b *bridgeSMTPSettings) UseSSL() bool {
+	return b.b.vault.GetSMTPSSL()
+}
+
+func (b *bridgeSMTPSettings) Identifier() identifier.UserAgentUpdater {
+	return &bridgeUserAgentUpdater{Bridge: b.b}
 }

internal/bridge/smtp_backend.go

@@ -1,96 +0,0 @@
-// Copyright (c) 2023 Proton AG
-//
-// This file is part of Proton Mail Bridge.
-//
-// Proton Mail Bridge is free software: you can redistribute it and/or modify
-// it under the terms of the GNU General Public License as published by
-// the Free Software Foundation, either version 3 of the License, or
-// (at your option) any later version.
-//
-// Proton Mail Bridge is distributed in the hope that it will be useful,
-// but WITHOUT ANY WARRANTY; without even the implied warranty of
-// MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
-// GNU General Public License for more details.
-//
-// You should have received a copy of the GNU General Public License
-// along with Proton Mail Bridge.  If not, see <https://www.gnu.org/licenses/>.
-
-package bridge
-
-import (
-	"fmt"
-	"io"
-
-	"github.com/ProtonMail/proton-bridge/v3/internal/safe"
-	"github.com/emersion/go-smtp"
-)
-
-type smtpBackend struct {
-	*Bridge
-}
-
-type smtpSession struct {
-	*Bridge
-
-	userID string
-	authID string
-
-	from string
-	to   []string
-}
-
-func (be *smtpBackend) NewSession(*smtp.Conn) (smtp.Session, error) {
-	return &smtpSession{Bridge: be.Bridge}, nil
-}
-
-func (s *smtpSession) AuthPlain(username, password string) error {
-	return safe.RLockRet(func() error {
-		for _, user := range s.users {
-			addrID, err := user.CheckAuth(username, []byte(password))
-			if err != nil {
-				continue
-			}
-
-			s.userID = user.ID()
-			s.authID = addrID
-
-			return nil
-		}
-
-		return fmt.Errorf("invalid username or password")
-	}, s.usersLock)
-}
-
-func (s *smtpSession) Reset() {
-	s.from = ""
-	s.to = nil
-}
-
-func (s *smtpSession) Logout() error {
-	s.Reset()
-	return nil
-}
-
-func (s *smtpSession) Mail(from string, opts *smtp.MailOptions) error {
-	s.from = from
-	return nil
-}
-
-func (s *smtpSession) Rcpt(to string) error {
-	if len(to) > 0 {
-		s.to = append(s.to, to)
-	}
-
-	return nil
-}
-
-func (s *smtpSession) Data(r io.Reader) error {
-	return safe.RLockRet(func() error {
-		user, ok := s.users[s.userID]
-		if !ok {
-			return ErrNoSuchUser
-		}
-
-		return user.SendMail(s.authID, s.from, s.to, r)
-	}, s.usersLock)
-}

internal/bridge/sync_test.go

@@ -1,4 +1,4 @@
-// Copyright (c) 2023 Proton AG
+// Copyright (c) 2025 Proton AG
 //
 // This file is part of Proton Mail Bridge.
 //
@@ -21,19 +21,23 @@ import (
 	"context"
 	"fmt"
 	"io"
+	"net/http"
 	"os"
 	"path/filepath"
 	"runtime"
+	"strings"
 	"sync/atomic"
 	"testing"
 	"time"
 
+	"github.com/ProtonMail/gluon/async"
 	"github.com/ProtonMail/gluon/rfc822"
 	"github.com/ProtonMail/go-proton-api"
 	"github.com/ProtonMail/go-proton-api/server"
 	"github.com/ProtonMail/proton-bridge/v3/internal/bridge"
 	"github.com/ProtonMail/proton-bridge/v3/internal/constants"
 	"github.com/ProtonMail/proton-bridge/v3/internal/events"
+	"github.com/ProtonMail/proton-bridge/v3/internal/services/imapservice"
 	"github.com/bradenaw/juniper/iterator"
 	"github.com/bradenaw/juniper/stream"
 	"github.com/bradenaw/juniper/xslices"
@@ -79,7 +83,7 @@ func TestBridge_Sync(t *testing.T) {
 			require.NoError(t, err)
 			require.True(t, info.State == bridge.Connected)
 
-			client, err := client.Dial(fmt.Sprintf("%v:%v", constants.Host, b.GetIMAPPort()))
+			client, err := eventuallyDial(fmt.Sprintf("%v:%v", constants.Host, b.GetIMAPPort()))
 			require.NoError(t, err)
 			require.NoError(t, client.Login(info.Addresses[0], string(info.BridgePass)))
 			defer func() { _ = client.Logout() }()
@@ -111,15 +115,6 @@ func TestBridge_Sync(t *testing.T) {
 				info, err := b.GetUserInfo(userID)
 				require.NoError(t, err)
 				require.True(t, info.State == bridge.Connected)
-
-				client, err := client.Dial(fmt.Sprintf("%v:%v", constants.Host, b.GetIMAPPort()))
-				require.NoError(t, err)
-				require.NoError(t, client.Login(info.Addresses[0], string(info.BridgePass)))
-				defer func() { _ = client.Logout() }()
-
-				status, err := client.Select(`Folders/folder`, false)
-				require.NoError(t, err)
-				require.Less(t, status.Messages, uint32(numMsg))
 			}
 
 			// Remove the network limit, allowing the sync to finish.
@@ -135,7 +130,7 @@ func TestBridge_Sync(t *testing.T) {
 				require.NoError(t, err)
 				require.True(t, info.State == bridge.Connected)
 
-				client, err := client.Dial(fmt.Sprintf("%v:%v", constants.Host, b.GetIMAPPort()))
+				client, err := eventuallyDial(fmt.Sprintf("%v:%v", constants.Host, b.GetIMAPPort()))
 				require.NoError(t, err)
 				require.NoError(t, client.Login(info.Addresses[0], string(info.BridgePass)))
 				defer func() { _ = client.Logout() }()
@@ -186,7 +181,7 @@ func _TestBridge_Sync_BadMessage(t *testing.T) { //nolint:unused,deadcode
 			require.NoError(t, err)
 			require.True(t, info.State == bridge.Connected)
 
-			client, err := client.Dial(fmt.Sprintf("%v:%v", constants.Host, b.GetIMAPPort()))
+			client, err := eventuallyDial(fmt.Sprintf("%v:%v", constants.Host, b.GetIMAPPort()))
 			require.NoError(t, err)
 			require.NoError(t, client.Login(info.Addresses[0], string(info.BridgePass)))
 			defer func() { _ = client.Logout() }()
@@ -237,7 +232,7 @@ func TestBridge_SyncWithOngoingEvents(t *testing.T) {
 		var total uint64
 
 		// The initial user should be fully synced.
-		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, mocks *bridge.Mocks) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
 			syncCh, done := chToType[events.Event, events.SyncFinished](bridge.GetEvents(events.SyncFinished{}))
 			defer done()
 
@@ -251,7 +246,7 @@ func TestBridge_SyncWithOngoingEvents(t *testing.T) {
 		})
 
 		// Now let's remove the user and stop the network at 2/3 of the data.
-		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, mocks *bridge.Mocks) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
 			require.NoError(t, bridge.DeleteUser(ctx, userID))
 		})
 
@@ -259,28 +254,22 @@ func TestBridge_SyncWithOngoingEvents(t *testing.T) {
 		netCtl.SetReadLimit(2 * total / 3)
 
 		// Login the user; its sync should fail.
-		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(b *bridge.Bridge, mocks *bridge.Mocks) {
-			{
-				syncCh, done := chToType[events.Event, events.SyncFailed](b.GetEvents(events.SyncFailed{}))
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(b *bridge.Bridge, _ *bridge.Mocks) {
+			syncCh, done := chToType[events.Event, events.SyncFinished](b.GetEvents(events.SyncFinished{}))
 			defer done()
 
+			{
+				syncFailedCh, syncFailedDone := chToType[events.Event, events.SyncFailed](b.GetEvents(events.SyncFailed{}))
+				defer syncFailedDone()
+
 				userID, err := b.LoginFull(ctx, "imap", password, nil, nil)
 				require.NoError(t, err)
 
-				require.Equal(t, userID, (<-syncCh).UserID)
+				require.Equal(t, userID, (<-syncFailedCh).UserID)
 
 				info, err := b.GetUserInfo(userID)
 				require.NoError(t, err)
 				require.True(t, info.State == bridge.Connected)
-
-				client, err := client.Dial(fmt.Sprintf("%v:%v", constants.Host, b.GetIMAPPort()))
-				require.NoError(t, err)
-				require.NoError(t, client.Login(info.Addresses[0], string(info.BridgePass)))
-				defer func() { _ = client.Logout() }()
-
-				status, err := client.Select(`Folders/folder`, false)
-				require.NoError(t, err)
-				require.Less(t, status.Messages, uint32(numMsg))
 			}
 
 			// Create a new mailbox and move that last 1/3 of the messages into it to simulate user
@@ -299,28 +288,18 @@ func TestBridge_SyncWithOngoingEvents(t *testing.T) {
 
 			// Remove the network limit, allowing the sync to finish.
 			netCtl.SetReadLimit(0)
-
 			{
-				syncCh, done := chToType[events.Event, events.SyncFinished](b.GetEvents(events.SyncFinished{}))
-				defer done()
-
 				require.Equal(t, userID, (<-syncCh).UserID)
 
 				info, err := b.GetUserInfo(userID)
 				require.NoError(t, err)
 				require.True(t, info.State == bridge.Connected)
 
-				client, err := client.Dial(fmt.Sprintf("%v:%v", constants.Host, b.GetIMAPPort()))
+				client, err := eventuallyDial(fmt.Sprintf("%v:%v", constants.Host, b.GetIMAPPort()))
 				require.NoError(t, err)
 				require.NoError(t, client.Login(info.Addresses[0], string(info.BridgePass)))
 				defer func() { _ = client.Logout() }()
 
-				status, err := client.Select(`Folders/folder`, false)
-				require.NoError(t, err)
-				// Original folder should have more than 0 messages and less than the total.
-				require.Greater(t, status.Messages, uint32(0))
-				require.Less(t, status.Messages, uint32(numMsg))
-
 				// Check that the new messages arrive in the right location.
 				require.Eventually(t, func() bool {
 					status, err := client.Select(`Folders/folder2`, true)
@@ -338,6 +317,379 @@ func TestBridge_SyncWithOngoingEvents(t *testing.T) {
 	}, server.WithTLS(false))
 }
 
+func TestBridge_CanProcessEventsDuringSync(t *testing.T) {
+	numMsg := 1 << 8
+
+	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, storeKey []byte) {
+		userID, addrID, err := s.CreateUser("imap", password)
+		require.NoError(t, err)
+
+		labelID, err := s.CreateLabel(userID, "folder", "", proton.LabelTypeFolder)
+		require.NoError(t, err)
+
+		withClient(ctx, t, s, "imap", password, func(ctx context.Context, c *proton.Client) {
+			createNumMessages(ctx, t, c, addrID, labelID, numMsg)
+		})
+
+		// Simulate 429 to prevent sync from progressing.
+		s.AddStatusHook(func(request *http.Request) (int, bool) {
+			if strings.Contains(request.URL.Path, "/mail/v4/messages/") {
+				return http.StatusTooManyRequests, true
+			}
+
+			return 0, false
+		})
+
+		// The initial user should be fully synced.
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
+			syncStartedCh, syncStartedDone := chToType[events.Event, events.SyncStarted](bridge.GetEvents(events.SyncStarted{}))
+			defer syncStartedDone()
+
+			addressCreatedCh, addressCreatedDone := chToType[events.Event, events.UserAddressCreated](bridge.GetEvents(events.UserAddressCreated{}))
+			defer addressCreatedDone()
+
+			userID, err := bridge.LoginFull(ctx, "imap", password, nil, nil)
+			require.NoError(t, err)
+
+			require.Equal(t, userID, (<-syncStartedCh).UserID)
+
+			// Create a new address
+			newAddress := "foo@proton.ch"
+			addrID, err := s.CreateAddress(userID, newAddress, password)
+			require.NoError(t, err)
+
+			event := <-addressCreatedCh
+			require.Equal(t, userID, event.UserID)
+			require.Equal(t, newAddress, event.Email)
+			require.Equal(t, addrID, event.AddressID)
+		})
+	}, server.WithTLS(false))
+}
+
+func TestBridge_RefreshDuringSyncRestartSync(t *testing.T) {
+	numMsg := 1 << 8
+
+	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, storeKey []byte) {
+		userID, addrID, err := s.CreateUser("imap", password)
+		require.NoError(t, err)
+
+		labelID, err := s.CreateLabel(userID, "folder", "", proton.LabelTypeFolder)
+		require.NoError(t, err)
+
+		withClient(ctx, t, s, "imap", password, func(ctx context.Context, c *proton.Client) {
+			createNumMessages(ctx, t, c, addrID, labelID, numMsg)
+		})
+
+		var refreshPerformed atomic.Bool
+		refreshPerformed.Store(false)
+
+		// Simulate 429 to prevent sync from progressing.
+		s.AddStatusHook(func(request *http.Request) (int, bool) {
+			if strings.Contains(request.URL.Path, "/mail/v4/messages/") {
+				if !refreshPerformed.Load() {
+					return http.StatusTooManyRequests, true
+				}
+			}
+
+			return 0, false
+		})
+
+		// The initial user should be fully synced.
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
+			syncCh, done := chToType[events.Event, events.SyncFinished](bridge.GetEvents(events.SyncFinished{}))
+			defer done()
+
+			userID, err := bridge.LoginFull(ctx, "imap", password, nil, nil)
+			require.NoError(t, err)
+
+			syncStartedCh, syncStartedDone := chToType[events.Event, events.SyncStarted](bridge.GetEvents(events.SyncStarted{}))
+			defer syncStartedDone()
+
+			require.Equal(t, userID, (<-syncStartedCh).UserID)
+
+			require.NoError(t, err, s.RefreshUser(userID, proton.RefreshMail))
+			require.Equal(t, userID, (<-syncStartedCh).UserID)
+			refreshPerformed.Store(true)
+
+			require.Equal(t, userID, (<-syncCh).UserID)
+		})
+	}, server.WithTLS(false))
+}
+
+func TestBridge_EventReplayAfterSyncHasFinished(t *testing.T) {
+	numMsg := 1 << 8
+
+	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, storeKey []byte) {
+		userID, addrID, err := s.CreateUser("imap", password)
+		require.NoError(t, err)
+
+		labelID, err := s.CreateLabel(userID, "folder", "", proton.LabelTypeFolder)
+		require.NoError(t, err)
+
+		withClient(ctx, t, s, "imap", password, func(ctx context.Context, c *proton.Client) {
+			createNumMessages(ctx, t, c, addrID, labelID, numMsg)
+		})
+
+		addrID1, err := s.CreateAddress(userID, "foo@proton.ch", password)
+		require.NoError(t, err)
+
+		var allowSyncToProgress atomic.Bool
+		allowSyncToProgress.Store(false)
+
+		// Simulate 429 to prevent sync from progressing.
+		s.AddStatusHook(func(request *http.Request) (int, bool) {
+			if request.Method == "GET" && strings.Contains(request.URL.Path, "/mail/v4/messages/") {
+				if !allowSyncToProgress.Load() {
+					return http.StatusTooManyRequests, true
+				}
+			}
+
+			return 0, false
+		})
+
+		// The initial user should be fully synced.
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
+			syncCh, done := chToType[events.Event, events.SyncFinished](bridge.GetEvents(events.SyncFinished{}))
+			defer done()
+
+			syncStartedCh, syncStartedDone := chToType[events.Event, events.SyncStarted](bridge.GetEvents(events.SyncStarted{}))
+			defer syncStartedDone()
+
+			addressCreatedCh, addressCreatedDone := chToType[events.Event, events.UserAddressCreated](bridge.GetEvents(events.UserAddressCreated{}))
+			defer addressCreatedDone()
+
+			userID, err := bridge.LoginFull(ctx, "imap", password, nil, nil)
+			require.NoError(t, err)
+
+			require.Equal(t, userID, (<-syncStartedCh).UserID)
+
+			// create 20 more messages and move them to inbox
+			withClient(ctx, t, s, "imap", password, func(ctx context.Context, c *proton.Client) {
+				createNumMessages(ctx, t, c, addrID, proton.InboxLabel, 20)
+			})
+
+			// User AddrID2 event as a check point to see when the new address was created.
+			addrID2, err := s.CreateAddress(userID, "bar@proton.ch", password)
+			require.NoError(t, err)
+
+			allowSyncToProgress.Store(true)
+			require.Equal(t, userID, (<-syncCh).UserID)
+
+			// At most two events can be published, one for the first address, then for the second.
+			// if the second event is not `addrID2` then something went wrong.
+			event := <-addressCreatedCh
+			if event.AddressID == addrID1 {
+				event = <-addressCreatedCh
+			}
+
+			require.Equal(t, addrID2, event.AddressID)
+
+			info, err := bridge.GetUserInfo(userID)
+			require.NoError(t, err)
+
+			client, err := eventuallyDial(fmt.Sprintf("%v:%v", constants.Host, bridge.GetIMAPPort()))
+			require.NoError(t, err)
+			require.NoError(t, client.Login(info.Addresses[0], string(info.BridgePass)))
+			defer func() { _ = client.Logout() }()
+
+			// Finally check if the 20 messages are in INBOX.
+			status, err := client.Status("INBOX", []imap.StatusItem{imap.StatusMessages})
+			require.NoError(t, err)
+			require.Equal(t, uint32(20), status.Messages)
+
+			// Finally check if the numMsg are in the folder.
+			status, err = client.Status("Folders/folder", []imap.StatusItem{imap.StatusMessages})
+			require.NoError(t, err)
+			require.Equal(t, uint32(numMsg), status.Messages)
+		})
+	}, server.WithTLS(false))
+}
+
+func TestBridge_MessageCreateDuringSync(t *testing.T) {
+	numMsg := 1 << 8
+
+	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, storeKey []byte) {
+		userID, addrID, err := s.CreateUser("imap", password)
+		require.NoError(t, err)
+
+		labelID, err := s.CreateLabel(userID, "folder", "", proton.LabelTypeFolder)
+		require.NoError(t, err)
+
+		withClient(ctx, t, s, "imap", password, func(ctx context.Context, c *proton.Client) {
+			createNumMessages(ctx, t, c, addrID, labelID, numMsg)
+		})
+
+		var allowSyncToProgress atomic.Bool
+		allowSyncToProgress.Store(false)
+
+		// Simulate 429 to prevent sync from progressing.
+		s.AddStatusHook(func(request *http.Request) (int, bool) {
+			if request.Method == "GET" && strings.Contains(request.URL.Path, "/mail/v4/messages/") {
+				if !allowSyncToProgress.Load() {
+					return http.StatusTooManyRequests, true
+				}
+			}
+
+			return 0, false
+		})
+
+		// The initial user should be fully synced.
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
+			syncStartedCh, syncStartedDone := chToType[events.Event, events.SyncStarted](bridge.GetEvents(events.SyncStarted{}))
+			defer syncStartedDone()
+
+			addressCreatedCh, addressCreatedDone := chToType[events.Event, events.UserAddressCreated](bridge.GetEvents(events.UserAddressCreated{}))
+			defer addressCreatedDone()
+
+			userID, err := bridge.LoginFull(ctx, "imap", password, nil, nil)
+			require.NoError(t, err)
+
+			require.Equal(t, userID, (<-syncStartedCh).UserID)
+
+			// create 20 more messages and move them to inbox
+			withClient(ctx, t, s, "imap", password, func(ctx context.Context, c *proton.Client) {
+				createNumMessages(ctx, t, c, addrID, proton.InboxLabel, 20)
+			})
+
+			// User AddrID2 event as a check point to see when the new address was created.
+			addrID, err := s.CreateAddress(userID, "bar@proton.ch", password)
+			require.NoError(t, err)
+
+			// At most two events can be published, one for the first address, then for the second.
+			// if the second event is not `addrID` then something went wrong.
+			event := <-addressCreatedCh
+			require.Equal(t, addrID, event.AddressID)
+			allowSyncToProgress.Store(true)
+
+			info, err := bridge.GetUserInfo(userID)
+			require.NoError(t, err)
+
+			client, err := eventuallyDial(fmt.Sprintf("%v:%v", constants.Host, bridge.GetIMAPPort()))
+			require.NoError(t, err)
+			require.NoError(t, client.Login(info.Addresses[0], string(info.BridgePass)))
+			defer func() { _ = client.Logout() }()
+
+			require.Eventually(t, func() bool {
+				// Finally check if the 20 messages are in INBOX.
+				status, err := client.Status("INBOX", []imap.StatusItem{imap.StatusMessages})
+				require.NoError(t, err)
+
+				return uint32(20) == status.Messages
+			}, 10*time.Second, time.Second)
+		})
+	}, server.WithTLS(false))
+}
+
+func TestBridge_CorruptedVaultClearsPreviousIMAPSyncState(t *testing.T) {
+	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, vaultKey []byte) {
+		userID, addrID, err := s.CreateUser("imap", password)
+		require.NoError(t, err)
+
+		labelID, err := s.CreateLabel(userID, "folder", "", proton.LabelTypeFolder)
+		require.NoError(t, err)
+
+		withClient(ctx, t, s, "imap", password, func(ctx context.Context, c *proton.Client) {
+			createNumMessages(ctx, t, c, addrID, labelID, 100)
+		})
+
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, vaultKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
+			syncCh, done := chToType[events.Event, events.SyncFinished](bridge.GetEvents(events.SyncFinished{}))
+			defer done()
+
+			var err error
+
+			userID, err = bridge.LoginFull(context.Background(), "imap", password, nil, nil)
+			require.NoError(t, err)
+
+			// Wait for sync to finish
+			require.Equal(t, userID, (<-syncCh).UserID)
+		})
+
+		settingsPath, err := locator.ProvideSettingsPath()
+		require.NoError(t, err)
+
+		syncConfigPath, err := locator.ProvideIMAPSyncConfigPath()
+		require.NoError(t, err)
+
+		syncStatePath := imapservice.GetSyncConfigPath(syncConfigPath, userID)
+		// Check sync state is complete
+		{
+			state, err := imapservice.NewSyncState(syncStatePath)
+			require.NoError(t, err)
+			syncStatus, err := state.GetSyncStatus(context.Background())
+			require.NoError(t, err)
+			require.True(t, syncStatus.IsComplete())
+		}
+
+		// corrupt the vault
+		require.NoError(t, os.WriteFile(filepath.Join(settingsPath, "vault.enc"), []byte("Trash!"), 0o600))
+
+		// Bridge starts but can't find the gluon database dir; there should be no error.
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, vaultKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
+			_, err := bridge.LoginFull(context.Background(), "imap", password, nil, nil)
+			require.NoError(t, err)
+		})
+
+		// Check sync state is reset.
+		{
+			state, err := imapservice.NewSyncState(syncStatePath)
+			require.NoError(t, err)
+			syncStatus, err := state.GetSyncStatus(context.Background())
+			require.NoError(t, err)
+			require.False(t, syncStatus.IsComplete())
+		}
+	})
+}
+
+func TestBridge_AddressOrderChangeDuringSyncInCombinedModeDoesNotTriggerBadEventOnNewMessage(t *testing.T) {
+	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, storeKey []byte) {
+		// Create a user.
+		userID, addrID, err := s.CreateUser("user", password)
+		require.NoError(t, err)
+
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
+			userInfoChanged, done := chToType[events.Event, events.UserChanged](bridge.GetEvents(events.UserChanged{}))
+			defer done()
+
+			withClient(ctx, t, s, "user", password, func(ctx context.Context, c *proton.Client) {
+				createNumMessages(ctx, t, c, addrID, proton.InboxLabel, 300)
+			})
+
+			_, err := bridge.LoginFull(ctx, "user", password, nil, nil)
+			require.NoError(t, err)
+
+			info, err := bridge.GetUserInfo(userID)
+			require.NoError(t, err)
+			require.Equal(t, 1, len(info.Addresses))
+			require.Equal(t, info.Addresses[0], "user@proton.local")
+
+			addrID2, err := s.CreateAddress(userID, "foo@"+s.GetDomain(), password)
+			require.NoError(t, err)
+
+			require.NoError(t, s.SetAddressOrder(userID, []string{addrID2, addrID}))
+
+			withClient(ctx, t, s, "user", password, func(ctx context.Context, c *proton.Client) {
+				createNumMessages(ctx, t, c, addrID2, proton.InboxLabel, 1)
+			})
+
+			// Since we can't intercept events at this time, we sleep for a bit to make sure the
+			// new message does not get combined into the event below. This ensures the newly created
+			// goes through the full code flow which triggered the original bad event.
+			time.Sleep(time.Second)
+			require.NoError(t, s.SetAddressOrder(userID, []string{addrID, addrID2}))
+
+			for i := 0; i < 2; i++ {
+				select {
+				case <-ctx.Done():
+					return
+				case e := <-userInfoChanged:
+					require.Equal(t, userID, e.UserID)
+				}
+			}
+		})
+	})
+}
+
 func withClient(ctx context.Context, t *testing.T, s *server.Server, username string, password []byte, fn func(context.Context, *proton.Client)) { //nolint:unparam
 	m := proton.New(
 		proton.WithHostURL(s.GetHostURL()),
@@ -351,7 +703,7 @@ func withClient(ctx context.Context, t *testing.T, s *server.Server, username st
 	fn(ctx, c)
 }
 
-func clientFetch(client *client.Client, mailbox string) ([]*imap.Message, error) {
+func clientFetch(client *client.Client, mailbox string, extraItems ...imap.FetchItem) ([]*imap.Message, error) {
 	status, err := client.Select(mailbox, false)
 	if err != nil {
 		return nil, err
@@ -363,10 +715,13 @@ func clientFetch(client *client.Client, mailbox string) ([]*imap.Message, error)
 
 	resCh := make(chan *imap.Message)
 
+	fetchItems := []imap.FetchItem{imap.FetchFlags, imap.FetchEnvelope, imap.FetchUid, imap.FetchBodyStructure, "BODY.PEEK[]"}
+	fetchItems = append(fetchItems, extraItems...)
+
 	go func() {
 		if err := client.Fetch(
 			&imap.SeqSet{Set: []imap.Seq{{Start: 1, Stop: status.Messages}}},
-			[]imap.FetchItem{imap.FetchFlags, imap.FetchEnvelope, imap.FetchUid, "BODY.PEEK[]"},
+			fetchItems,
 			resCh,
 		); err != nil {
 			panic(err)
@@ -413,6 +768,10 @@ func createNumMessages(ctx context.Context, t *testing.T, c *proton.Client, addr
 }
 
 func createMessages(ctx context.Context, t *testing.T, c *proton.Client, addrID, labelID string, messages ...[]byte) []string {
+	return createMessagesWithFlags(ctx, t, c, addrID, labelID, 0, messages...)
+}
+
+func createMessagesWithFlags(ctx context.Context, t *testing.T, c *proton.Client, addrID, labelID string, flags proton.MessageFlag, messages ...[]byte) []string {
 	user, err := c.GetUser(ctx)
 	require.NoError(t, err)
 
@@ -425,13 +784,20 @@ func createMessages(ctx context.Context, t *testing.T, c *proton.Client, addrID,
 	keyPass, err := salt.SaltForKey(password, user.Keys.Primary().ID)
 	require.NoError(t, err)
 
-	_, addrKRs, err := proton.Unlock(user, addr, keyPass)
+	_, addrKRs, err := proton.Unlock(user, addr, keyPass, async.NoopPanicHandler{})
 	require.NoError(t, err)
 
 	_, ok := addrKRs[addrID]
 	require.True(t, ok)
 
-	res, err := stream.Collect(ctx, c.ImportMessages(
+	var msgFlags proton.MessageFlag
+	if flags == 0 {
+		msgFlags = proton.MessageFlagReceived
+	} else {
+		msgFlags = flags
+	}
+
+	str, err := c.ImportMessages(
 		ctx,
 		addrKRs[addrID],
 		runtime.NumCPU(),
@@ -441,12 +807,15 @@ func createMessages(ctx context.Context, t *testing.T, c *proton.Client, addrID,
 				Metadata: proton.ImportMetadata{
 					AddressID: addrID,
 					LabelIDs:  []string{labelID},
-					Flags:     proton.MessageFlagReceived,
+					Flags:     msgFlags,
 				},
 				Message: message,
 			}
 		})...,
-	))
+	)
+	require.NoError(t, err)
+
+	res, err := stream.Collect(ctx, str)
 	require.NoError(t, err)
 
 	return xslices.Map(res, func(res proton.ImportRes) string {

internal/bridge/sync_unix_test.go

@@ -0,0 +1,82 @@
+// Copyright (c) 2025 Proton AG
+//
+// This file is part of Proton Mail Bridge.
+//
+// Proton Mail Bridge is free software: you can redistribute it and/or modify
+// it under the terms of the GNU General Public License as published by
+// the Free Software Foundation, either version 3 of the License, or
+// (at your option) any later version.
+//
+// Proton Mail Bridge is distributed in the hope that it will be useful,
+// but WITHOUT ANY WARRANTY; without even the implied warranty of
+// MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+// GNU General Public License for more details.
+//
+// You should have received a copy of the GNU General Public License
+// along with Proton Mail Bridge.  If not, see <https://www.gnu.org/licenses/>.
+
+//go:build !windows
+
+package bridge_test
+
+import (
+	"context"
+	"syscall"
+	"testing"
+
+	"github.com/ProtonMail/go-proton-api"
+	"github.com/ProtonMail/go-proton-api/server"
+	"github.com/ProtonMail/proton-bridge/v3/internal/bridge"
+	"github.com/ProtonMail/proton-bridge/v3/internal/events"
+	"github.com/stretchr/testify/require"
+)
+
+// Disabled due to flakiness.
+func _TestBridge_SyncExistsWithErrorWhenTooManyFilesAreOpen(t *testing.T) { //nolint:unused
+	var rlimitCurrent syscall.Rlimit
+
+	require.NoError(t, syscall.Getrlimit(syscall.RLIMIT_NOFILE, &rlimitCurrent))
+
+	// Restore RLimit for Process at the end of this test
+	defer func() {
+		require.NoError(t, syscall.Setrlimit(syscall.RLIMIT_NOFILE, &rlimitCurrent))
+	}()
+
+	rlimit := syscall.Rlimit{
+		Max: 100,
+		Cur: 100,
+	}
+
+	require.NoError(t, syscall.Setrlimit(syscall.RLIMIT_NOFILE, &rlimit))
+
+	numMsg := 1 << 8
+
+	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, storeKey []byte) {
+		userID, addrID, err := s.CreateUser("imap", password)
+		require.NoError(t, err)
+
+		labelID, err := s.CreateLabel(userID, "folder", "", proton.LabelTypeFolder)
+		require.NoError(t, err)
+
+		withClient(ctx, t, s, "imap", password, func(ctx context.Context, c *proton.Client) {
+			createNumMessages(ctx, t, c, addrID, labelID, numMsg)
+		})
+
+		// The initial user should be fully synced.
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
+			syncCh, done := bridge.GetEvents(events.SyncFailed{})
+			defer done()
+
+			userID, err := bridge.LoginFull(ctx, "imap", password, nil, nil)
+			require.NoError(t, err)
+
+			evt := <-syncCh
+			switch e := evt.(type) {
+			case events.SyncFailed:
+				require.Equal(t, userID, e.UserID)
+			default:
+				require.Fail(t, "Expected events.SyncFailed{}")
+			}
+		})
+	}, server.WithTLS(false))
+}

internal/bridge/tls.go

@@ -1,4 +1,4 @@
-// Copyright (c) 2023 Proton AG
+// Copyright (c) 2025 Proton AG
 //
 // This file is part of Proton Mail Bridge.
 //
@@ -18,5 +18,9 @@
 package bridge
 
 func (bridge *Bridge) GetBridgeTLSCert() ([]byte, []byte) {
-	return bridge.vault.GetBridgeTLSCert(), bridge.vault.GetBridgeTLSKey()
+	return bridge.vault.GetBridgeTLSCert()
+}
+
+func (bridge *Bridge) SetBridgeTLSCertPath(certPath, keyPath string) error {
+	return bridge.vault.SetBridgeTLSCertPath(certPath, keyPath)
 }

internal/bridge/types.go

@@ -1,4 +1,4 @@
-// Copyright (c) 2023 Proton AG
+// Copyright (c) 2025 Proton AG
 //
 // This file is part of Proton Mail Bridge.
 //
@@ -30,14 +30,10 @@ type Locator interface {
 	ProvideGluonDataPath() (string, error)
 	GetLicenseFilePath() string
 	GetDependencyLicensesLink() string
-	Clear() error
-}
-
-type Identifier interface {
-	GetUserAgent() string
-	HasClient() bool
-	SetClient(name, version string)
-	SetPlatform(platform string)
+	Clear(...string) error
+	ProvideIMAPSyncConfigPath() (string, error)
+	ProvideUnleashCachePath() (string, error)
+	ProvideNotificationsCachePath() (string, error)
 }
 
 type ProxyController interface {
@@ -56,6 +52,9 @@ type Autostarter interface {
 }
 
 type Updater interface {
-	GetVersionInfo(context.Context, updater.Downloader, updater.Channel) (updater.VersionInfo, error)
-	InstallUpdate(context.Context, updater.Downloader, updater.VersionInfo) error
+	GetVersionInfoLegacy(context.Context, updater.Downloader, updater.Channel) (updater.VersionInfoLegacy, error)
+	InstallUpdateLegacy(context.Context, updater.Downloader, updater.VersionInfoLegacy) error
+	RemoveOldUpdates() error
+	GetVersionInfo(context.Context, updater.Downloader) (updater.VersionInfo, error)
+	InstallUpdate(context.Context, updater.Downloader, updater.Release) error
 }

internal/bridge/unleash_test.go

@@ -0,0 +1,90 @@
+// Copyright (c) 2025 Proton AG
+//
+// This file is part of Proton Mail Bridge.
+//
+// Proton Mail Bridge is free software: you can redistribute it and/or modify
+// it under the terms of the GNU General Public License as published by
+// the Free Software Foundation, either version 3 of the License, or
+// (at your option) any later version.
+//
+// Proton Mail Bridge is distributed in the hope that it will be useful,
+// but WITHOUT ANY WARRANTY; without even the implied warranty of
+// MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+// GNU General Public License for more details.
+//
+// You should have received a copy of the GNU General Public License
+// along with Proton Mail Bridge. If not, see <https://www.gnu.org/licenses/>.
+
+package bridge_test
+
+import (
+	"context"
+	"testing"
+	"time"
+
+	"github.com/ProtonMail/go-proton-api"
+	"github.com/ProtonMail/go-proton-api/server"
+	"github.com/ProtonMail/proton-bridge/v3/internal/bridge"
+	"github.com/ProtonMail/proton-bridge/v3/internal/unleash"
+	"github.com/stretchr/testify/require"
+)
+
+func Test_UnleashService(t *testing.T) {
+	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, storeKey []byte) {
+		unleash.ModifyPollPeriodAndJitter(500*time.Millisecond, 0)
+
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(b *bridge.Bridge, _ *bridge.Mocks) {
+			// Initial startup assumes there is no cached feature flags.
+			require.Equal(t, b.GetFeatureFlagValue("test-1"), false)
+			require.Equal(t, b.GetFeatureFlagValue("test-2"), false)
+			require.Equal(t, b.GetFeatureFlagValue("test-3"), false)
+
+			s.PushFeatureFlag("test-1")
+			s.PushFeatureFlag("test-2")
+
+			// Wait for poll.
+			time.Sleep(time.Millisecond * 700)
+			require.Equal(t, b.GetFeatureFlagValue("test-1"), true)
+			require.Equal(t, b.GetFeatureFlagValue("test-2"), true)
+			require.Equal(t, b.GetFeatureFlagValue("test-3"), false)
+
+			s.PushFeatureFlag("test-3")
+			time.Sleep(time.Millisecond * 700) // Wait for poll again
+			require.Equal(t, b.GetFeatureFlagValue("test-1"), true)
+			require.Equal(t, b.GetFeatureFlagValue("test-2"), true)
+			require.Equal(t, b.GetFeatureFlagValue("test-3"), true)
+		})
+
+		// Wait for Bridge to close.
+		time.Sleep(time.Millisecond * 500)
+
+		// Second instance should have a feature flag cache file available. Therefore, all of the flags should evaluate to true on startup.
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(b *bridge.Bridge, _ *bridge.Mocks) {
+			require.Equal(t, b.GetFeatureFlagValue("test-1"), true)
+			require.Equal(t, b.GetFeatureFlagValue("test-2"), true)
+			require.Equal(t, b.GetFeatureFlagValue("test-3"), true)
+
+			s.DeleteFeatureFlags()
+
+			require.Equal(t, b.GetFeatureFlagValue("test-1"), true)
+			require.Equal(t, b.GetFeatureFlagValue("test-2"), true)
+			require.Equal(t, b.GetFeatureFlagValue("test-3"), true)
+
+			time.Sleep(time.Millisecond * 700)
+
+			require.Equal(t, b.GetFeatureFlagValue("test-1"), false)
+			require.Equal(t, b.GetFeatureFlagValue("test-2"), false)
+			require.Equal(t, b.GetFeatureFlagValue("test-3"), false)
+
+			s.PushFeatureFlag("test-3")
+			require.Equal(t, b.GetFeatureFlagValue("test-1"), false)
+			require.Equal(t, b.GetFeatureFlagValue("test-2"), false)
+			require.Equal(t, b.GetFeatureFlagValue("test-3"), false)
+
+			time.Sleep(time.Millisecond * 700)
+			require.Equal(t, b.GetFeatureFlagValue("test-1"), false)
+			require.Equal(t, b.GetFeatureFlagValue("test-2"), false)
+			require.Equal(t, b.GetFeatureFlagValue("test-3"), true)
+		})
+	})
+}

internal/bridge/updates.go

@@ -1,4 +1,4 @@
-// Copyright (c) 2023 Proton AG
+// Copyright (c) 2025 Proton AG
 //
 // This file is part of Proton Mail Bridge.
 //
@@ -21,33 +21,168 @@ import (
 	"context"
 	"errors"
 
+	"github.com/Masterminds/semver/v3"
+	"github.com/ProtonMail/gluon/reporter"
 	"github.com/ProtonMail/proton-bridge/v3/internal/events"
 	"github.com/ProtonMail/proton-bridge/v3/internal/safe"
 	"github.com/ProtonMail/proton-bridge/v3/internal/updater"
+	"github.com/elastic/go-sysinfo"
 	"github.com/sirupsen/logrus"
+	"golang.org/x/exp/slices"
 )
 
 func (bridge *Bridge) CheckForUpdates() {
 	bridge.goUpdate()
 }
 
-func (bridge *Bridge) InstallUpdate(version updater.VersionInfo) {
-	log := logrus.WithFields(logrus.Fields{
-		"version": version.Version,
-		"current": bridge.curVersion,
-		"channel": bridge.vault.GetUpdateChannel(),
-	})
+func (bridge *Bridge) InstallUpdateLegacy(version updater.VersionInfoLegacy) {
+	bridge.installChLegacy <- installJobLegacy{version: version, silent: false}
+}
 
-	select {
-	case bridge.installCh <- installJob{version: version, silent: false}:
-		log.Info("The update will be installed manually")
-
-	default:
-		log.Info("An update is already being installed")
-	}
+func (bridge *Bridge) InstallUpdate(release updater.Release) {
+	bridge.installCh <- installJob{Release: release, Silent: false}
 }
 
 func (bridge *Bridge) handleUpdate(version updater.VersionInfo) {
+	updateChannel := bridge.vault.GetUpdateChannel()
+	updateRollout := bridge.vault.GetUpdateRollout()
+	autoUpdateEnabled := bridge.vault.GetAutoUpdate()
+
+	checkSystemVersion := true
+	hostInfo, err := sysinfo.Host()
+	// If we're unable to get host system information we skip the update's minimum/maximum OS version checks
+	if err != nil {
+		checkSystemVersion = false
+		logrus.WithError(err).Error("Failed to obtain host system info while handling updates")
+		if reporterErr := bridge.reporter.ReportMessageWithContext(
+			"Failed to obtain host system info while handling updates",
+			reporter.Context{"error": err},
+		); reporterErr != nil {
+			logrus.WithError(reporterErr).Error("Failed to report update error")
+		}
+	}
+
+	if len(version.Releases) > 0 {
+		// Update latest is only used to update the release notes and landing page URL
+		bridge.publish(events.UpdateLatest{Release: version.Releases[0]})
+	}
+
+	// minAutoUpdateEvent - used to determine the highest compatible update that satisfies the Minimum Bridge version
+	minAutoUpdateEvent := events.UpdateAvailable{
+		Release:    updater.Release{Version: &semver.Version{}},
+		Compatible: false,
+		Silent:     false,
+	}
+
+	// We assume that the version file is always created in descending order
+	// where newer versions are prepended to the top of the releases
+	// The logic for checking update eligibility is as follows:
+	// 1. Check release channel.
+	// 2. Check whether release version is greater.
+	// 3. Check if rollout is larger.
+	// 4. Check OS Version restrictions (provided that restrictions are provided, and we can extract the OS version).
+	// 5. Check Minimum Compatible Bridge Version.
+	// 6. Check if an update package is provided.
+	// 7. Check auto-update.
+	for _, release := range version.Releases {
+		log := logrus.WithFields(logrus.Fields{
+			"current":               bridge.curVersion,
+			"channel":               updateChannel,
+			"update_version":        release.Version,
+			"update_channel":        release.ReleaseCategory,
+			"update_min_auto":       release.MinAuto,
+			"update_rollout":        release.RolloutProportion,
+			"update_min_os_version": release.SystemVersion.Minimum,
+			"update_max_os_version": release.SystemVersion.Maximum,
+		})
+
+		log.Debug("Checking update release")
+
+		if !release.ReleaseCategory.UpdateEligible(updateChannel) {
+			log.Debug("Update does not satisfy update channel requirement")
+			continue
+		}
+
+		if !release.Version.GreaterThan(bridge.curVersion) {
+			log.Debug("Update version is not greater than current version")
+			continue
+		}
+
+		if release.RolloutProportion < updateRollout {
+			log.Debug("Update has not been rolled out yet")
+			continue
+		}
+
+		if checkSystemVersion {
+			shouldContinue, err := release.SystemVersion.IsHostVersionEligible(log, hostInfo, bridge.getHostVersion)
+			if err != nil && shouldContinue {
+				log.WithError(err).Error(
+					"Failed to verify host system version compatibility during release check." +
+						"Error is non-fatal continuing with checks",
+				)
+			} else if err != nil {
+				log.WithError(err).Error("Failed to verify host system version compatibility during update check")
+				continue
+			}
+
+			if !shouldContinue {
+				log.Debug("Host version does not satisfy system requirements for update")
+				continue
+			}
+		}
+
+		if release.MinAuto != nil && bridge.curVersion.LessThan(release.MinAuto) {
+			log.Debug("Update is available but is incompatible with this Bridge version")
+			if release.Version.GreaterThan(minAutoUpdateEvent.Release.Version) {
+				minAutoUpdateEvent.Release = release
+			}
+			continue
+		}
+
+		// Check if we have a provided installer package
+		if found := slices.IndexFunc(release.File, func(file updater.File) bool {
+			return file.Identifier == updater.PackageIdentifier
+		}); found == -1 {
+			log.Error("Update is available but does not contain update package")
+
+			if reporterErr := bridge.reporter.ReportMessageWithContext(
+				"Available update does not contain update package",
+				reporter.Context{"update_version": release.Version},
+			); reporterErr != nil {
+				log.WithError(reporterErr).Error("Failed to report update error")
+			}
+
+			continue
+		}
+
+		if !autoUpdateEnabled {
+			log.Info("An update is available but auto-update is disabled")
+			bridge.publish(events.UpdateAvailable{
+				Release:    release,
+				Compatible: true,
+				Silent:     false,
+			})
+			return
+		}
+
+		// If we've gotten to this point that means an automatic update is available and we should install it
+		safe.RLock(func() {
+			bridge.installCh <- installJob{Release: release, Silent: true}
+		}, bridge.newVersionLock)
+
+		return
+	}
+
+	// If there's a release with a minAuto requirement that we satisfy (alongside all other checks)
+	// then notify the user that a manual update is needed
+	if !minAutoUpdateEvent.Release.Version.Equal(&semver.Version{}) {
+		bridge.publish(minAutoUpdateEvent)
+	}
+
+	bridge.publish(events.UpdateNotAvailable{})
+}
+
+func (bridge *Bridge) handleUpdateLegacy(version updater.VersionInfoLegacy) {
 	log := logrus.WithFields(logrus.Fields{
 		"version": version.Version,
 		"current": bridge.curVersion,
@@ -55,7 +190,7 @@ func (bridge *Bridge) handleUpdate(version updater.VersionInfo) {
 	})
 
 	bridge.publish(events.UpdateLatest{
-		Version: version,
+		VersionLegacy: version,
 	})
 
 	switch {
@@ -73,7 +208,7 @@ func (bridge *Bridge) handleUpdate(version updater.VersionInfo) {
 		log.Info("An update is available but is incompatible with this version")
 
 		bridge.publish(events.UpdateAvailable{
-			Version:    version,
+			VersionLegacy: version,
 			Compatible:    false,
 			Silent:        false,
 		})
@@ -82,34 +217,24 @@ func (bridge *Bridge) handleUpdate(version updater.VersionInfo) {
 		log.Info("An update is available but auto-update is disabled")
 
 		bridge.publish(events.UpdateAvailable{
-			Version:    version,
+			VersionLegacy: version,
 			Compatible:    true,
 			Silent:        false,
 		})
 
 	default:
 		safe.RLock(func() {
-			if version.Version.GreaterThan(bridge.newVersion) {
-				log.Info("An update is available")
-
-				select {
-				case bridge.installCh <- installJob{version: version, silent: true}:
-					log.Info("The update will be installed silently")
-
-				default:
-					log.Info("An update is already being installed")
-				}
-			}
+			bridge.installChLegacy <- installJobLegacy{version: version, silent: true}
 		}, bridge.newVersionLock)
 	}
 }
 
-type installJob struct {
-	version updater.VersionInfo
+type installJobLegacy struct {
+	version updater.VersionInfoLegacy
 	silent  bool
 }
 
-func (bridge *Bridge) installUpdate(ctx context.Context, job installJob) {
+func (bridge *Bridge) installUpdateLegacy(ctx context.Context, job installJobLegacy) {
 	safe.Lock(func() {
 		log := logrus.WithFields(logrus.Fields{
 			"version": job.version.Version,
@@ -117,20 +242,32 @@ func (bridge *Bridge) installUpdate(ctx context.Context, job installJob) {
 			"channel": bridge.vault.GetUpdateChannel(),
 		})
 
+		if !job.version.Version.GreaterThan(bridge.newVersion) {
+			return
+		}
+
+		log.WithField("silent", job.silent).Info("An update is available")
+
 		bridge.publish(events.UpdateAvailable{
-			Version:    job.version,
+			VersionLegacy: job.version,
 			Compatible:    true,
 			Silent:        job.silent,
 		})
 
-		bridge.publish(events.UpdateInstalling{
-			Version: job.version,
-			Silent:  job.silent,
-		})
-
-		err := bridge.updater.InstallUpdate(ctx, bridge.api, job.version)
+		err := bridge.updater.InstallUpdateLegacy(ctx, bridge.api, job.version)
 
 		switch {
+		case errors.Is(err, updater.ErrDownloadVerify):
+			// BRIDGE-207: if download or verification fails, we do not want to trigger a manual update. We report in the log and to Sentry
+			// and we fail silently.
+			log.WithError(err).Error("The update could not be installed, but we will fail silently")
+			if reporterErr := bridge.reporter.ReportMessageWithContext(
+				"Cannot download or verify update",
+				reporter.Context{"error": err},
+			); reporterErr != nil {
+				log.WithError(reporterErr).Error("Failed to report update error")
+			}
+
 		case errors.Is(err, updater.ErrUpdateAlreadyInstalled):
 			log.Info("The update was already installed")
 
@@ -138,15 +275,16 @@ func (bridge *Bridge) installUpdate(ctx context.Context, job installJob) {
 			log.WithError(err).Error("The update could not be installed")
 
 			bridge.publish(events.UpdateFailed{
-				Version: job.version,
+				VersionLegacy: job.version,
 				Silent:        job.silent,
 				Error:         err,
 			})
+
 		default:
 			log.Info("The update was installed successfully")
 
 			bridge.publish(events.UpdateInstalled{
-				Version: job.version,
+				VersionLegacy: job.version,
 				Silent:        job.silent,
 			})
 
@@ -154,3 +292,80 @@ func (bridge *Bridge) installUpdate(ctx context.Context, job installJob) {
 		}
 	}, bridge.newVersionLock)
 }
+
+type installJob struct {
+	Release updater.Release
+	Silent  bool
+}
+
+func (bridge *Bridge) installUpdate(ctx context.Context, job installJob) {
+	safe.Lock(func() {
+		log := logrus.WithFields(logrus.Fields{
+			"version": job.Release.Version,
+			"current": bridge.curVersion,
+			"channel": bridge.vault.GetUpdateChannel(),
+		})
+
+		if !job.Release.Version.GreaterThan(bridge.newVersion) {
+			return
+		}
+
+		log.WithField("silent", job.Silent).Info("An update is available")
+
+		bridge.publish(events.UpdateAvailable{
+			Release:    job.Release,
+			Compatible: true,
+			Silent:     job.Silent,
+		})
+
+		err := bridge.updater.InstallUpdate(ctx, bridge.api, job.Release)
+		switch {
+		case errors.Is(err, updater.ErrReleaseUpdatePackageMissing):
+			log.WithError(err).Error("The update could not be installed but we will fail silently")
+			if reporterErr := bridge.reporter.ReportExceptionWithContext(
+				"Cannot download update, update package is missing",
+				reporter.Context{"error": err},
+			); reporterErr != nil {
+				log.WithError(reporterErr).Error("Failed to report update error")
+			}
+		case errors.Is(err, updater.ErrDownloadVerify):
+			// BRIDGE-207: if download or verification fails, we do not want to trigger a manual update. We report in the log and to Sentry
+			// and we fail silently.
+			log.WithError(err).Error("The update could not be installed, but we will fail silently")
+			if reporterErr := bridge.reporter.ReportMessageWithContext(
+				"Cannot download or verify update",
+				reporter.Context{"error": err},
+			); reporterErr != nil {
+				log.WithError(reporterErr).Error("Failed to report update error")
+			}
+
+		case errors.Is(err, updater.ErrUpdateAlreadyInstalled):
+			log.Info("The update was already installed")
+
+		case err != nil:
+			log.WithError(err).Error("The update could not be installed")
+
+			bridge.publish(events.UpdateFailed{
+				Release: job.Release,
+				Silent:  job.Silent,
+				Error:   err,
+			})
+
+		default:
+			log.Info("The update was installed successfully")
+
+			bridge.publish(events.UpdateInstalled{
+				Release: job.Release,
+				Silent:  job.Silent,
+			})
+
+			bridge.newVersion = job.Release.Version
+		}
+	}, bridge.newVersionLock)
+}
+
+func (bridge *Bridge) RemoveOldUpdates() {
+	if err := bridge.updater.RemoveOldUpdates(); err != nil {
+		logrus.WithError(err).Error("Remove old updates fails")
+	}
+}

internal/bridge/updates_test.go

@@ -0,0 +1,700 @@
+// Copyright (c) 2025 Proton AG
+//
+// This file is part of Proton Mail Bridge.
+//
+// Proton Mail Bridge is free software: you can redistribute it and/or modify
+// it under the terms of the GNU General Public License as published by
+// the Free Software Foundation, either version 3 of the License, or
+// (at your option) any later version.
+//
+// Proton Mail Bridge is distributed in the hope that it will be useful,
+// but WITHOUT ANY WARRANTY; without even the implied warranty of
+// MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+// GNU General Public License for more details.
+//
+// You should have received a copy of the GNU General Public License
+// along with Proton Mail Bridge. If not, see <https://www.gnu.org/licenses/>.
+
+package bridge_test
+
+import (
+	"context"
+	"runtime"
+	"testing"
+	"time"
+
+	"github.com/Masterminds/semver/v3"
+	"github.com/ProtonMail/go-proton-api"
+	"github.com/ProtonMail/go-proton-api/server"
+	bridgePkg "github.com/ProtonMail/proton-bridge/v3/internal/bridge"
+	"github.com/ProtonMail/proton-bridge/v3/internal/events"
+	"github.com/ProtonMail/proton-bridge/v3/internal/updater"
+	"github.com/ProtonMail/proton-bridge/v3/internal/updater/versioncompare"
+	"github.com/elastic/go-sysinfo/types"
+	"github.com/stretchr/testify/require"
+)
+
+// NOTE: we always assume the highest version is always the first in the release json array
+
+func Test_Update_BetaEligible(t *testing.T) {
+	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridgePkg.Locator, vaultKey []byte) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, vaultKey, func(bridge *bridgePkg.Bridge, mocks *bridgePkg.Mocks) {
+			updateCh, done := bridge.GetEvents(events.UpdateInstalled{})
+			defer done()
+
+			err := bridge.SetUpdateChannel(updater.EarlyChannel)
+			require.NoError(t, err)
+
+			bridge.SetCurrentVersionTest(semver.MustParse("2.1.1"))
+
+			expectedRelease := updater.Release{
+				ReleaseCategory:   updater.EarlyAccessReleaseCategory,
+				Version:           semver.MustParse("2.1.2"),
+				SystemVersion:     versioncompare.SystemVersion{},
+				RolloutProportion: 1.0,
+				MinAuto:           &semver.Version{},
+				File: []updater.File{
+					{
+						URL:        "RANDOM_INSTALLER_URL",
+						Identifier: updater.InstallerIdentifier,
+					},
+					{
+						URL:        "RANDOM_PACKAGE_URL",
+						Identifier: updater.PackageIdentifier,
+					},
+				},
+			}
+
+			updaterData := updater.VersionInfo{Releases: []updater.Release{
+				expectedRelease,
+			}}
+
+			go func() {
+				time.Sleep(1 * time.Second)
+				mocks.Updater.SetLatestVersion(updaterData)
+				bridge.CheckForUpdates()
+			}()
+
+			select {
+			case update := <-updateCh:
+				require.Equal(t, events.UpdateInstalled{
+					Release: expectedRelease,
+					Silent:  true,
+				}, update)
+			case <-time.After(2 * time.Second):
+				t.Fatal("timeout waiting for update")
+			}
+		})
+	})
+}
+
+func Test_Update_Stable(t *testing.T) {
+	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridgePkg.Locator, vaultKey []byte) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, vaultKey, func(bridge *bridgePkg.Bridge, mocks *bridgePkg.Mocks) {
+			updateCh, done := bridge.GetEvents(events.UpdateInstalled{})
+			defer done()
+
+			err := bridge.SetUpdateChannel(updater.StableChannel)
+			require.NoError(t, err)
+
+			bridge.SetCurrentVersionTest(semver.MustParse("2.1.1"))
+
+			expectedRelease := updater.Release{
+				ReleaseCategory:   updater.StableReleaseCategory,
+				Version:           semver.MustParse("2.1.3"),
+				SystemVersion:     versioncompare.SystemVersion{},
+				RolloutProportion: 1.0,
+				MinAuto:           &semver.Version{},
+				File: []updater.File{
+					{
+						URL:        "RANDOM_INSTALLER_URL",
+						Identifier: updater.InstallerIdentifier,
+					},
+					{
+						URL:        "RANDOM_PACKAGE_URL",
+						Identifier: updater.PackageIdentifier,
+					},
+				},
+			}
+
+			updaterData := updater.VersionInfo{Releases: []updater.Release{
+				{
+					ReleaseCategory:   updater.EarlyAccessReleaseCategory,
+					Version:           semver.MustParse("2.1.4"),
+					SystemVersion:     versioncompare.SystemVersion{},
+					RolloutProportion: 1.0,
+					MinAuto:           &semver.Version{},
+					File: []updater.File{
+						{
+							URL:        "RANDOM_INSTALLER_URL",
+							Identifier: updater.InstallerIdentifier,
+						},
+						{
+							URL:        "RANDOM_PACKAGE_URL",
+							Identifier: updater.PackageIdentifier,
+						},
+					},
+				},
+				expectedRelease,
+			}}
+
+			mocks.Updater.SetLatestVersion(updaterData)
+
+			bridge.CheckForUpdates()
+
+			require.Equal(t, events.UpdateInstalled{
+				Release: expectedRelease,
+				Silent:  true,
+			}, <-updateCh)
+		})
+	})
+}
+
+func Test_Update_CurrentReleaseNewest(t *testing.T) {
+	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridgePkg.Locator, vaultKey []byte) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, vaultKey, func(bridge *bridgePkg.Bridge, mocks *bridgePkg.Mocks) {
+			updateCh, done := bridge.GetEvents(events.UpdateNotAvailable{})
+			defer done()
+
+			err := bridge.SetUpdateChannel(updater.StableChannel)
+			require.NoError(t, err)
+
+			bridge.SetCurrentVersionTest(semver.MustParse("2.1.5"))
+
+			expectedRelease := updater.Release{
+				ReleaseCategory:   updater.StableReleaseCategory,
+				Version:           semver.MustParse("2.1.3"),
+				SystemVersion:     versioncompare.SystemVersion{},
+				RolloutProportion: 1.0,
+				MinAuto:           &semver.Version{},
+				File: []updater.File{
+					{
+						URL:        "RANDOM_INSTALLER_URL",
+						Identifier: updater.InstallerIdentifier,
+					},
+					{
+						URL:        "RANDOM_PACKAGE_URL",
+						Identifier: updater.PackageIdentifier,
+					},
+				},
+			}
+
+			updaterData := updater.VersionInfo{Releases: []updater.Release{
+				{
+					ReleaseCategory:   updater.EarlyAccessReleaseCategory,
+					Version:           semver.MustParse("2.1.4"),
+					SystemVersion:     versioncompare.SystemVersion{},
+					RolloutProportion: 1.0,
+					MinAuto:           &semver.Version{},
+					File: []updater.File{
+						{
+							URL:        "RANDOM_INSTALLER_URL",
+							Identifier: updater.InstallerIdentifier,
+						},
+						{
+							URL:        "RANDOM_PACKAGE_URL",
+							Identifier: updater.PackageIdentifier,
+						},
+					},
+				},
+				expectedRelease,
+			}}
+
+			mocks.Updater.SetLatestVersion(updaterData)
+			bridge.CheckForUpdates()
+
+			require.Equal(t, events.UpdateNotAvailable{}, <-updateCh)
+		})
+	})
+}
+
+func Test_Update_NotRolledOutYet(t *testing.T) {
+	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridgePkg.Locator, vaultKey []byte) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, vaultKey, func(bridge *bridgePkg.Bridge, mocks *bridgePkg.Mocks) {
+			require.NoError(t, bridge.SetUpdateChannel(updater.EarlyChannel))
+			bridge.SetCurrentVersionTest(semver.MustParse("2.0.0"))
+			require.NoError(t, bridge.SetRolloutPercentageTest(1.0))
+
+			updaterData := updater.VersionInfo{Releases: []updater.Release{
+				{
+					ReleaseCategory:   updater.StableReleaseCategory,
+					Version:           semver.MustParse("2.1.5"),
+					SystemVersion:     versioncompare.SystemVersion{},
+					RolloutProportion: 0.5,
+					MinAuto:           &semver.Version{},
+					File: []updater.File{
+						{
+							URL:        "RANDOM_INSTALLER_URL",
+							Identifier: updater.InstallerIdentifier,
+						},
+						{
+							URL:        "RANDOM_PACKAGE_URL",
+							Identifier: updater.PackageIdentifier,
+						},
+					},
+				},
+				{
+					ReleaseCategory:   updater.StableReleaseCategory,
+					Version:           semver.MustParse("2.1.4"),
+					SystemVersion:     versioncompare.SystemVersion{},
+					RolloutProportion: 0.5,
+					MinAuto:           &semver.Version{},
+					File: []updater.File{
+						{
+							URL:        "RANDOM_INSTALLER_URL",
+							Identifier: updater.InstallerIdentifier,
+						},
+						{
+							URL:        "RANDOM_PACKAGE_URL",
+							Identifier: updater.PackageIdentifier,
+						},
+					},
+				},
+			}}
+
+			mocks.Updater.SetLatestVersion(updaterData)
+
+			updateCh, done := bridge.GetEvents(events.UpdateNotAvailable{})
+			defer done()
+
+			bridge.CheckForUpdates()
+
+			require.Equal(t, events.UpdateNotAvailable{}, <-updateCh)
+		})
+	})
+}
+
+func Test_Update_CheckOSVersion_NoUpdate(t *testing.T) {
+	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridgePkg.Locator, vaultKey []byte) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, vaultKey, func(bridge *bridgePkg.Bridge, mocks *bridgePkg.Mocks) {
+			require.NoError(t, bridge.SetAutoUpdate(true))
+			require.NoError(t, bridge.SetUpdateChannel(updater.StableChannel))
+
+			currentBridgeVersion := semver.MustParse("2.1.5")
+			bridge.SetCurrentVersionTest(currentBridgeVersion)
+
+			// Override the OS version check
+			bridge.SetHostVersionGetterTest(func(_ types.Host) string {
+				return "10.0.0"
+			})
+
+			updateNotAvailableCh, done := bridge.GetEvents(events.UpdateNotAvailable{})
+			defer done()
+
+			updateCh, updateChDone := bridge.GetEvents(events.UpdateInstalled{})
+			defer updateChDone()
+
+			expectedRelease := updater.Release{
+				ReleaseCategory: updater.StableReleaseCategory,
+				Version:         semver.MustParse("2.4.0"),
+				SystemVersion: versioncompare.SystemVersion{
+					Minimum: "12.0.0",
+					Maximum: "13.0.0",
+				},
+				RolloutProportion: 1.0,
+				File: []updater.File{
+					{
+						URL:        "RANDOM_INSTALLER_URL",
+						Identifier: updater.InstallerIdentifier,
+					},
+					{
+						URL:        "RANDOM_PACKAGE_URL",
+						Identifier: updater.PackageIdentifier,
+					},
+				},
+			}
+
+			updaterData := updater.VersionInfo{Releases: []updater.Release{
+				expectedRelease,
+				{
+					ReleaseCategory: updater.StableReleaseCategory,
+					Version:         semver.MustParse("2.3.0"),
+					SystemVersion: versioncompare.SystemVersion{
+						Minimum: "10.1.0",
+						Maximum: "11.5",
+					},
+					RolloutProportion: 1.0,
+					File: []updater.File{
+						{
+							URL:        "RANDOM_INSTALLER_URL",
+							Identifier: updater.InstallerIdentifier,
+						},
+						{
+							URL:        "RANDOM_PACKAGE_URL",
+							Identifier: updater.PackageIdentifier,
+						},
+					},
+				},
+			}}
+
+			mocks.Updater.SetLatestVersion(updaterData)
+
+			bridge.CheckForUpdates()
+
+			if runtime.GOOS == "darwin" {
+				require.Equal(t, events.UpdateNotAvailable{}, <-updateNotAvailableCh)
+			} else {
+				require.Equal(t, events.UpdateInstalled{
+					Release: expectedRelease,
+					Silent:  true,
+				}, <-updateCh)
+			}
+		})
+	})
+}
+
+func Test_Update_CheckOSVersion_HasUpdate(t *testing.T) {
+	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridgePkg.Locator, vaultKey []byte) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, vaultKey, func(bridge *bridgePkg.Bridge, mocks *bridgePkg.Mocks) {
+			require.NoError(t, bridge.SetAutoUpdate(true))
+			require.NoError(t, bridge.SetUpdateChannel(updater.StableChannel))
+
+			updateCh, done := bridge.GetEvents(events.UpdateInstalled{})
+			defer done()
+
+			currentBridgeVersion := semver.MustParse("2.1.5")
+			bridge.SetCurrentVersionTest(currentBridgeVersion)
+
+			// Override the OS version check
+			bridge.SetHostVersionGetterTest(func(_ types.Host) string {
+				return "10.0.0"
+			})
+
+			expectedUpdateRelease := updater.Release{
+				ReleaseCategory: updater.StableReleaseCategory,
+				Version:         semver.MustParse("2.2.0"),
+				SystemVersion: versioncompare.SystemVersion{
+					Minimum: "10.0.0",
+					Maximum: "10.1.12",
+				},
+				RolloutProportion: 1.0,
+				File: []updater.File{
+					{
+						URL:        "RANDOM_INSTALLER_URL",
+						Identifier: updater.InstallerIdentifier,
+					},
+					{
+						URL:        "RANDOM_PACKAGE_URL",
+						Identifier: updater.PackageIdentifier,
+					},
+				},
+			}
+
+			expectedUpdateReleaseWindowsLinux := updater.Release{
+				ReleaseCategory: updater.StableReleaseCategory,
+				Version:         semver.MustParse("2.4.0"),
+				SystemVersion: versioncompare.SystemVersion{
+					Minimum: "12.0.0",
+				},
+				RolloutProportion: 1.0,
+				File: []updater.File{
+					{
+						URL:        "RANDOM_INSTALLER_URL",
+						Identifier: updater.InstallerIdentifier,
+					},
+					{
+						URL:        "RANDOM_PACKAGE_URL",
+						Identifier: updater.PackageIdentifier,
+					},
+				},
+			}
+
+			updaterData := updater.VersionInfo{Releases: []updater.Release{
+				expectedUpdateReleaseWindowsLinux,
+				{
+					ReleaseCategory: updater.StableReleaseCategory,
+					Version:         semver.MustParse("2.3.0"),
+					SystemVersion: versioncompare.SystemVersion{
+						Minimum: "11.0.0",
+					},
+					RolloutProportion: 1.0,
+					File: []updater.File{
+						{
+							URL:        "RANDOM_INSTALLER_URL",
+							Identifier: updater.InstallerIdentifier,
+						},
+						{
+							URL:        "RANDOM_PACKAGE_URL",
+							Identifier: updater.PackageIdentifier,
+						},
+					},
+				},
+				expectedUpdateRelease,
+				{
+					ReleaseCategory:   updater.StableReleaseCategory,
+					Version:           semver.MustParse("2.1.0"),
+					SystemVersion:     versioncompare.SystemVersion{},
+					RolloutProportion: 1.0,
+					File: []updater.File{
+						{
+							URL:        "RANDOM_INSTALLER_URL",
+							Identifier: updater.InstallerIdentifier,
+						},
+						{
+							URL:        "RANDOM_PACKAGE_URL",
+							Identifier: updater.PackageIdentifier,
+						},
+					},
+				},
+			}}
+
+			mocks.Updater.SetLatestVersion(updaterData)
+
+			bridge.CheckForUpdates()
+
+			if runtime.GOOS == "darwin" {
+				require.Equal(t, events.UpdateInstalled{
+					Release: expectedUpdateRelease,
+					Silent:  true,
+				}, <-updateCh)
+			} else {
+				require.Equal(t, events.UpdateInstalled{
+					Release: expectedUpdateReleaseWindowsLinux,
+					Silent:  true,
+				}, <-updateCh)
+			}
+		})
+	})
+}
+
+func Test_Update_UpdateFromMinVer_UpdateAvailable(t *testing.T) {
+	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridgePkg.Locator, vaultKey []byte) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, vaultKey, func(bridge *bridgePkg.Bridge, mocks *bridgePkg.Mocks) {
+			require.NoError(t, bridge.SetAutoUpdate(true))
+			require.NoError(t, bridge.SetUpdateChannel(updater.StableChannel))
+
+			currentBridgeVersion := semver.MustParse("2.1.5")
+			bridge.SetCurrentVersionTest(currentBridgeVersion)
+
+			updateCh, done := bridge.GetEvents(events.UpdateInstalled{})
+			defer done()
+
+			expectedUpdateRelease := updater.Release{
+				ReleaseCategory:   updater.StableReleaseCategory,
+				Version:           semver.MustParse("2.2.0"),
+				SystemVersion:     versioncompare.SystemVersion{},
+				RolloutProportion: 1.0,
+				MinAuto:           currentBridgeVersion,
+				File: []updater.File{
+					{
+						URL:        "RANDOM_INSTALLER_URL",
+						Identifier: updater.InstallerIdentifier,
+					},
+					{
+						URL:        "RANDOM_PACKAGE_URL",
+						Identifier: updater.PackageIdentifier,
+					},
+				},
+			}
+
+			updaterData := updater.VersionInfo{Releases: []updater.Release{
+				{
+					ReleaseCategory:   updater.StableReleaseCategory,
+					Version:           semver.MustParse("2.3.0"),
+					SystemVersion:     versioncompare.SystemVersion{},
+					RolloutProportion: 1.0,
+					MinAuto:           semver.MustParse("2.2.1"),
+					File: []updater.File{
+						{
+							URL:        "RANDOM_INSTALLER_URL",
+							Identifier: updater.InstallerIdentifier,
+						},
+						{
+							URL:        "RANDOM_PACKAGE_URL",
+							Identifier: updater.PackageIdentifier,
+						},
+					},
+				},
+				{
+					ReleaseCategory:   updater.StableReleaseCategory,
+					Version:           semver.MustParse("2.2.1"),
+					SystemVersion:     versioncompare.SystemVersion{},
+					RolloutProportion: 1.0,
+					MinAuto:           semver.MustParse("2.2.0"),
+					File: []updater.File{
+						{
+							URL:        "RANDOM_INSTALLER_URL",
+							Identifier: updater.InstallerIdentifier,
+						},
+						{
+							URL:        "RANDOM_PACKAGE_URL",
+							Identifier: updater.PackageIdentifier,
+						},
+					},
+				},
+				expectedUpdateRelease,
+			}}
+
+			mocks.Updater.SetLatestVersion(updaterData)
+
+			bridge.CheckForUpdates()
+
+			require.Equal(t, events.UpdateInstalled{
+				Release: expectedUpdateRelease,
+				Silent:  true,
+			}, <-updateCh)
+		})
+	})
+}
+
+// Test_Update_UpdateFromMinVer_NoCompatibleVersionForceManual -
+// if we have an update, but we don't satisfy minVersion, a manual update to the highest possible version should be performed.
+func Test_Update_UpdateFromMinVer_NoCompatibleVersionForceManual(t *testing.T) {
+	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridgePkg.Locator, vaultKey []byte) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, vaultKey, func(bridge *bridgePkg.Bridge, mocks *bridgePkg.Mocks) {
+			require.NoError(t, bridge.SetAutoUpdate(true))
+			require.NoError(t, bridge.SetUpdateChannel(updater.StableChannel))
+
+			currentBridgeVersion := semver.MustParse("2.1.5")
+			bridge.SetCurrentVersionTest(currentBridgeVersion)
+
+			updateCh, done := bridge.GetEvents(events.UpdateAvailable{})
+			defer done()
+
+			expectedUpdateRelease := updater.Release{
+				ReleaseCategory:   updater.StableReleaseCategory,
+				Version:           semver.MustParse("2.3.0"),
+				SystemVersion:     versioncompare.SystemVersion{},
+				RolloutProportion: 1.0,
+				MinAuto:           semver.MustParse("2.2.1"),
+				File: []updater.File{
+					{
+						URL:        "RANDOM_INSTALLER_URL",
+						Identifier: updater.InstallerIdentifier,
+					},
+					{
+						URL:        "RANDOM_PACKAGE_URL",
+						Identifier: updater.PackageIdentifier,
+					},
+				},
+			}
+
+			updaterData := updater.VersionInfo{Releases: []updater.Release{
+				{
+					ReleaseCategory:   updater.StableReleaseCategory,
+					Version:           semver.MustParse("2.2.1"),
+					SystemVersion:     versioncompare.SystemVersion{},
+					RolloutProportion: 1.0,
+					MinAuto:           semver.MustParse("2.2.0"),
+					File: []updater.File{
+						{
+							URL:        "RANDOM_INSTALLER_URL",
+							Identifier: updater.InstallerIdentifier,
+						},
+						{
+							URL:        "RANDOM_PACKAGE_URL",
+							Identifier: updater.PackageIdentifier,
+						},
+					},
+				},
+				{
+					ReleaseCategory:   updater.StableReleaseCategory,
+					Version:           semver.MustParse("2.2.0"),
+					SystemVersion:     versioncompare.SystemVersion{},
+					RolloutProportion: 1.0,
+					MinAuto:           semver.MustParse("2.1.6"),
+					File: []updater.File{
+						{
+							URL:        "RANDOM_INSTALLER_URL",
+							Identifier: updater.InstallerIdentifier,
+						},
+						{
+							URL:        "RANDOM_PACKAGE_URL",
+							Identifier: updater.PackageIdentifier,
+						},
+					},
+				},
+				expectedUpdateRelease,
+			}}
+
+			mocks.Updater.SetLatestVersion(updaterData)
+
+			bridge.CheckForUpdates()
+
+			require.Equal(t, events.UpdateAvailable{
+				Release:    expectedUpdateRelease,
+				Silent:     false,
+				Compatible: false,
+			}, <-updateCh)
+		})
+	})
+}
+
+// Test_Update_UpdateFromMinVer_NoCompatibleVersionForceManual_BetaMismatch - only Beta updates are available
+// nor do we satisfy the minVersion, we can't do anything in this case.
+func Test_Update_UpdateFromMinVer_NoCompatibleVersionForceManual_BetaMismatch(t *testing.T) {
+	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridgePkg.Locator, vaultKey []byte) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, vaultKey, func(bridge *bridgePkg.Bridge, mocks *bridgePkg.Mocks) {
+			require.NoError(t, bridge.SetAutoUpdate(true))
+			require.NoError(t, bridge.SetUpdateChannel(updater.StableChannel))
+
+			currentBridgeVersion := semver.MustParse("2.1.5")
+			bridge.SetCurrentVersionTest(currentBridgeVersion)
+
+			updateCh, done := bridge.GetEvents(events.UpdateNotAvailable{})
+			defer done()
+
+			expectedUpdateRelease := updater.Release{
+				ReleaseCategory:   updater.EarlyAccessReleaseCategory,
+				Version:           semver.MustParse("2.3.0"),
+				SystemVersion:     versioncompare.SystemVersion{},
+				RolloutProportion: 1.0,
+				MinAuto:           semver.MustParse("2.2.1"),
+				File: []updater.File{
+					{
+						URL:        "RANDOM_INSTALLER_URL",
+						Identifier: updater.InstallerIdentifier,
+					},
+					{
+						URL:        "RANDOM_PACKAGE_URL",
+						Identifier: updater.PackageIdentifier,
+					},
+				},
+			}
+
+			updaterData := updater.VersionInfo{Releases: []updater.Release{
+				{
+					ReleaseCategory:   updater.EarlyAccessReleaseCategory,
+					Version:           semver.MustParse("2.2.1"),
+					SystemVersion:     versioncompare.SystemVersion{},
+					RolloutProportion: 1.0,
+					MinAuto:           semver.MustParse("2.2.0"),
+					File: []updater.File{
+						{
+							URL:        "RANDOM_INSTALLER_URL",
+							Identifier: updater.InstallerIdentifier,
+						},
+						{
+							URL:        "RANDOM_PACKAGE_URL",
+							Identifier: updater.PackageIdentifier,
+						},
+					},
+				},
+				{
+					ReleaseCategory:   updater.EarlyAccessReleaseCategory,
+					Version:           semver.MustParse("2.2.0"),
+					SystemVersion:     versioncompare.SystemVersion{},
+					RolloutProportion: 1.0,
+					MinAuto:           semver.MustParse("2.1.6"),
+					File: []updater.File{
+						{
+							URL:        "RANDOM_INSTALLER_URL",
+							Identifier: updater.InstallerIdentifier,
+						},
+						{
+							URL:        "RANDOM_PACKAGE_URL",
+							Identifier: updater.PackageIdentifier,
+						},
+					},
+				},
+				expectedUpdateRelease,
+			}}
+
+			mocks.Updater.SetLatestVersion(updaterData)
+
+			bridge.CheckForUpdates()
+
+			require.Equal(t, events.UpdateNotAvailable{}, <-updateCh)
+		})
+	})
+}

internal/bridge/user.go

@@ -1,4 +1,4 @@
-// Copyright (c) 2023 Proton AG
+// Copyright (c) 2025 Proton AG
 //
 // This file is part of Proton Mail Bridge.
 //
@@ -23,19 +23,25 @@ import (
 	"fmt"
 	"runtime"
 
+	"github.com/ProtonMail/gluon/async"
 	"github.com/ProtonMail/gluon/imap"
+	"github.com/ProtonMail/gluon/reporter"
 	"github.com/ProtonMail/go-proton-api"
-	"github.com/ProtonMail/proton-bridge/v3/internal/async"
 	"github.com/ProtonMail/proton-bridge/v3/internal/events"
+	"github.com/ProtonMail/proton-bridge/v3/internal/hv"
 	"github.com/ProtonMail/proton-bridge/v3/internal/logging"
 	"github.com/ProtonMail/proton-bridge/v3/internal/safe"
+	"github.com/ProtonMail/proton-bridge/v3/internal/services/imapservice"
 	"github.com/ProtonMail/proton-bridge/v3/internal/try"
+	"github.com/ProtonMail/proton-bridge/v3/internal/unleash"
 	"github.com/ProtonMail/proton-bridge/v3/internal/user"
 	"github.com/ProtonMail/proton-bridge/v3/internal/vault"
 	"github.com/go-resty/resty/v2"
 	"github.com/sirupsen/logrus"
 )
 
+var logUser = logrus.WithField("pkg", "bridge/user") //nolint:gochecknoglobals
+
 type UserState int
 
 const (
@@ -44,6 +50,8 @@ const (
 	Connected
 )
 
+var ErrFailedToUnlock = errors.New("failed to unlock user keys")
+
 type UserInfo struct {
 	// UserID is the user's API ID.
 	UserID string
@@ -64,10 +72,10 @@ type UserInfo struct {
 	BridgePass []byte
 
 	// UsedSpace is the amount of space used by the user.
-	UsedSpace int
+	UsedSpace uint64
 
 	// MaxSpace is the total amount of space available to the user.
-	MaxSpace int
+	MaxSpace uint64
 }
 
 // GetUserIDs returns the IDs of all known users (authorized or not).
@@ -117,23 +125,28 @@ func (bridge *Bridge) QueryUserInfo(query string) (UserInfo, error) {
 }
 
 // LoginAuth begins the login process. It returns an authorized client that might need 2FA.
-func (bridge *Bridge) LoginAuth(ctx context.Context, username string, password []byte) (*proton.Client, proton.Auth, error) {
-	logrus.WithField("username", logging.Sensitive(username)).Info("Authorizing user for login")
+func (bridge *Bridge) LoginAuth(ctx context.Context, username string, password []byte, hvDetails *proton.APIHVDetails) (*proton.Client, proton.Auth, error) {
+	logUser.WithField("username", logging.Sensitive(username)).Info("Authorizing user for login")
 
 	if username == "crash@bandicoot" {
 		panic("Your wish is my command.. I crash!")
 	}
-
-	client, auth, err := bridge.api.NewClientWithLogin(ctx, username, password)
+	client, auth, err := bridge.api.NewClientWithLoginWithHVToken(ctx, username, password, hvDetails)
 	if err != nil {
+		if hv.IsHvRequest(err) {
+			logUser.WithFields(logrus.Fields{"username": logging.Sensitive(username),
+				"loginError": err.Error()}).Info("Human Verification requested for login")
+			return nil, proton.Auth{}, err
+		}
+
 		return nil, proton.Auth{}, fmt.Errorf("failed to create new API client: %w", err)
 	}
 
 	if ok := safe.RLockRet(func() bool { return mapHas(bridge.users, auth.UserID) }, bridge.usersLock); ok {
-		logrus.WithField("userID", auth.UserID).Warn("User already logged in")
+		logUser.WithField("userID", auth.UserID).Warn("User already logged in")
 
 		if err := client.AuthDelete(ctx); err != nil {
-			logrus.WithError(err).Warn("Failed to delete auth")
+			logUser.WithError(err).Warn("Failed to delete auth")
 		}
 
 		return nil, proton.Auth{}, ErrUserAlreadyLoggedIn
@@ -148,18 +161,23 @@ func (bridge *Bridge) LoginUser(
 	client *proton.Client,
 	auth proton.Auth,
 	keyPass []byte,
+	hvDetails *proton.APIHVDetails,
 ) (string, error) {
-	logrus.WithField("userID", auth.UserID).Info("Logging in authorized user")
+	logUser.WithField("userID", auth.UserID).Info("Logging in authorized user")
 
 	userID, err := try.CatchVal(
 		func() (string, error) {
-			return bridge.loginUser(ctx, client, auth.UID, auth.RefreshToken, keyPass)
-		},
-		func() error {
-			return client.AuthDelete(ctx)
+			return bridge.loginUser(ctx, client, auth.UID, auth.RefreshToken, keyPass, hvDetails)
 		},
 	)
+
 	if err != nil {
+		// Failure to unlock will allow retries, so we do not delete auth.
+		if !errors.Is(err, ErrFailedToUnlock) {
+			if deleteErr := client.AuthDelete(ctx); deleteErr != nil {
+				logUser.WithError(deleteErr).Error("Failed to delete auth")
+			}
+		}
 		return "", fmt.Errorf("failed to login user: %w", err)
 	}
 
@@ -180,15 +198,16 @@ func (bridge *Bridge) LoginFull(
 	getTOTP func() (string, error),
 	getKeyPass func() ([]byte, error),
 ) (string, error) {
-	logrus.WithField("username", logging.Sensitive(username)).Info("Performing full user login")
+	logUser.WithField("username", logging.Sensitive(username)).Info("Performing full user login")
 
-	client, auth, err := bridge.LoginAuth(ctx, username, password)
+	// (atanas) the following may need to be modified once HV is merged (its used only for testing; and depends on whether we will test HV related logic)
+	client, auth, err := bridge.LoginAuth(ctx, username, password, nil)
 	if err != nil {
 		return "", fmt.Errorf("failed to begin login process: %w", err)
 	}
 
 	if auth.TwoFA.Enabled&proton.HasTOTP != 0 {
-		logrus.WithField("userID", auth.UserID).Info("Requesting TOTP")
+		logUser.WithField("userID", auth.UserID).Info("Requesting TOTP")
 
 		totp, err := getTOTP()
 		if err != nil {
@@ -203,7 +222,7 @@ func (bridge *Bridge) LoginFull(
 	var keyPass []byte
 
 	if auth.PasswordMode == proton.TwoPasswordMode {
-		logrus.WithField("userID", auth.UserID).Info("Requesting mailbox password")
+		logUser.WithField("userID", auth.UserID).Info("Requesting mailbox password")
 
 		userKeyPass, err := getKeyPass()
 		if err != nil {
@@ -215,12 +234,21 @@ func (bridge *Bridge) LoginFull(
 		keyPass = password
 	}
 
-	return bridge.LoginUser(ctx, client, auth, keyPass)
+	userID, err := bridge.LoginUser(ctx, client, auth, keyPass, nil)
+	if err != nil {
+		if deleteErr := client.AuthDelete(ctx); deleteErr != nil {
+			logUser.WithError(err).Error("Failed to delete auth")
+		}
+
+		return "", err
+	}
+
+	return userID, nil
 }
 
 // LogoutUser logs out the given user.
 func (bridge *Bridge) LogoutUser(ctx context.Context, userID string) error {
-	logrus.WithField("userID", userID).Info("Logging out user")
+	logUser.WithField("userID", userID).Info("Logging out user")
 
 	return safe.LockRet(func() error {
 		user, ok := bridge.users[userID]
@@ -240,7 +268,12 @@ func (bridge *Bridge) LogoutUser(ctx context.Context, userID string) error {
 
 // DeleteUser deletes the given user.
 func (bridge *Bridge) DeleteUser(ctx context.Context, userID string) error {
-	logrus.WithField("userID", userID).Info("Deleting user")
+	logUser.WithField("userID", userID).Info("Deleting user")
+
+	syncConfigDir, err := bridge.locator.ProvideIMAPSyncConfigPath()
+	if err != nil {
+		return fmt.Errorf("failed to get sync config path")
+	}
 
 	return safe.LockRet(func() error {
 		if !bridge.vault.HasUser(userID) {
@@ -251,8 +284,12 @@ func (bridge *Bridge) DeleteUser(ctx context.Context, userID string) error {
 			bridge.logoutUser(ctx, user, true, true)
 		}
 
+		if err := imapservice.DeleteSyncState(syncConfigDir, userID); err != nil {
+			return fmt.Errorf("failed to delete use sync config")
+		}
+
 		if err := bridge.vault.DeleteUser(userID); err != nil {
-			logrus.WithError(err).Error("Failed to delete vault user")
+			logUser.WithError(err).Error("Failed to delete vault user")
 		}
 
 		bridge.publish(events.UserDeleted{
@@ -265,7 +302,7 @@ func (bridge *Bridge) DeleteUser(ctx context.Context, userID string) error {
 
 // SetAddressMode sets the address mode for the given user.
 func (bridge *Bridge) SetAddressMode(ctx context.Context, userID string, mode vault.AddressMode) error {
-	logrus.WithField("userID", userID).WithField("mode", mode).Info("Setting address mode")
+	logUser.WithField("userID", userID).WithField("mode", mode).Info("Setting address mode")
 
 	return safe.RLockRet(func() error {
 		user, ok := bridge.users[userID]
@@ -277,29 +314,63 @@ func (bridge *Bridge) SetAddressMode(ctx context.Context, userID string, mode va
 			return fmt.Errorf("address mode is already %q", mode)
 		}
 
-		if err := bridge.removeIMAPUser(ctx, user, true); err != nil {
-			return fmt.Errorf("failed to remove IMAP user: %w", err)
-		}
-
 		if err := user.SetAddressMode(ctx, mode); err != nil {
 			return fmt.Errorf("failed to set address mode: %w", err)
 		}
 
-		if err := bridge.addIMAPUser(ctx, user); err != nil {
-			return fmt.Errorf("failed to add IMAP user: %w", err)
-		}
-
 		bridge.publish(events.AddressModeChanged{
 			UserID:      userID,
 			AddressMode: mode,
 		})
 
+		var splitMode = false
+		for _, user := range bridge.users {
+			if user.GetAddressMode() == vault.SplitMode {
+				splitMode = true
+				break
+			}
+		}
+		bridge.heartbeat.SetSplitMode(splitMode)
+
 		return nil
 	}, bridge.usersLock)
 }
 
-func (bridge *Bridge) loginUser(ctx context.Context, client *proton.Client, authUID, authRef string, keyPass []byte) (string, error) {
-	apiUser, err := client.GetUser(ctx)
+// SendBadEventUserFeedback passes the feedback to the given user.
+func (bridge *Bridge) SendBadEventUserFeedback(_ context.Context, userID string, doResync bool) error {
+	logUser.WithField("userID", userID).WithField("doResync", doResync).Info("Passing bad event feedback to user")
+
+	return safe.RLockRet(func() error {
+		ctx := context.Background()
+
+		user, ok := bridge.users[userID]
+		if !ok {
+			if rerr := bridge.reporter.ReportMessageWithContext(
+				"Failed to handle event: feedback failed: no such user",
+				reporter.Context{"user_id": userID},
+			); rerr != nil {
+				logUser.WithError(rerr).Error("Failed to report feedback failure")
+			}
+
+			return ErrNoSuchUser
+		}
+
+		if doResync {
+			return user.BadEventFeedbackResync(ctx)
+		}
+
+		bridge.logoutUser(ctx, user, true, false)
+
+		bridge.publish(events.UserLoggedOut{
+			UserID: userID,
+		})
+
+		return nil
+	}, bridge.usersLock)
+}
+
+func (bridge *Bridge) loginUser(ctx context.Context, client *proton.Client, authUID, authRef string, keyPass []byte, hvDetails *proton.APIHVDetails) (string, error) {
+	apiUser, err := client.GetUserWithHV(ctx, hvDetails)
 	if err != nil {
 		return "", fmt.Errorf("failed to get API user: %w", err)
 	}
@@ -315,9 +386,9 @@ func (bridge *Bridge) loginUser(ctx context.Context, client *proton.Client, auth
 	}
 
 	if userKR, err := apiUser.Keys.Unlock(saltedKeyPass, nil); err != nil {
-		return "", fmt.Errorf("failed to unlock user keys: %w", err)
+		return "", fmt.Errorf("%w: %w", ErrFailedToUnlock, err)
 	} else if userKR.CountDecryptionEntities() == 0 {
-		return "", fmt.Errorf("failed to unlock user keys")
+		return "", ErrFailedToUnlock
 	}
 
 	if err := bridge.addUser(ctx, client, apiUser, authUID, authRef, saltedKeyPass, true); err != nil {
@@ -329,11 +400,11 @@ func (bridge *Bridge) loginUser(ctx context.Context, client *proton.Client, auth
 
 // loadUsers tries to load each user in the vault that isn't already loaded.
 func (bridge *Bridge) loadUsers(ctx context.Context) error {
-	logrus.WithField("count", len(bridge.vault.GetUserIDs())).Info("Loading users")
-	defer logrus.Info("Finished loading users")
+	logUser.WithField("count", len(bridge.vault.GetUserIDs())).Info("Loading users")
+	defer logUser.Info("Finished loading users")
 
 	return bridge.vault.ForUser(runtime.NumCPU(), func(user *vault.User) error {
-		log := logrus.WithField("userID", user.UserID())
+		log := logUser.WithField("userID", user.UserID())
 
 		if user.AuthUID() == "" {
 			log.Info("User is not connected (skipping)")
@@ -345,7 +416,7 @@ func (bridge *Bridge) loadUsers(ctx context.Context) error {
 			return nil
 		}
 
-		log.Info("Loading connected user")
+		log.WithField("mode", user.AddressMode()).Info("Loading connected user")
 
 		bridge.publish(events.UserLoading{
 			UserID: user.UserID(),
@@ -377,9 +448,10 @@ func (bridge *Bridge) loadUser(ctx context.Context, user *vault.User) error {
 		if apiErr := new(proton.APIError); errors.As(err, &apiErr) && (apiErr.Code == proton.AuthRefreshTokenInvalid) {
 			// The session cannot be refreshed, we sign out the user by clearing his auth secrets.
 			if err := user.Clear(); err != nil {
-				logrus.WithError(err).Warn("Failed to clear user secrets")
+				logUser.WithError(err).Warn("Failed to clear user secrets")
 			}
 		}
+
 		return fmt.Errorf("failed to create API client: %w", err)
 	}
 
@@ -419,26 +491,26 @@ func (bridge *Bridge) addUser(
 		return fmt.Errorf("failed to add vault user: %w", err)
 	}
 
-	if err := bridge.addUserWithVault(ctx, client, apiUser, vaultUser); err != nil {
+	if err := bridge.addUserWithVault(ctx, client, apiUser, vaultUser, isNew); err != nil {
 		if _, ok := err.(*resty.ResponseError); ok || isLogin {
-			logrus.WithError(err).Error("Failed to add user, clearing its secrets from vault")
+			logUser.WithError(err).Error("Failed to add user, clearing its secrets from vault")
 
 			if err := vaultUser.Clear(); err != nil {
-				logrus.WithError(err).Error("Failed to clear user secrets")
+				logUser.WithError(err).Error("Failed to clear user secrets")
 			}
 		} else {
-			logrus.WithError(err).Error("Failed to add user")
+			logUser.WithError(err).Error("Failed to add user")
 		}
 
 		if err := vaultUser.Close(); err != nil {
-			logrus.WithError(err).Error("Failed to close vault user")
+			logUser.WithError(err).Error("Failed to close vault user")
 		}
 
 		if isNew {
-			logrus.Warn("Deleting newly added vault user")
+			logUser.Warn("Deleting newly added vault user")
 
 			if err := bridge.vault.DeleteUser(apiUser.ID); err != nil {
-				logrus.WithError(err).Error("Failed to delete vault user")
+				logUser.WithError(err).Error("Failed to delete vault user")
 			}
 		}
 
@@ -454,40 +526,48 @@ func (bridge *Bridge) addUserWithVault(
 	client *proton.Client,
 	apiUser proton.User,
 	vault *vault.User,
+	isNew bool,
 ) error {
+	syncSettingsPath, err := bridge.locator.ProvideIMAPSyncConfigPath()
+	if err != nil {
+		return fmt.Errorf("failed to get IMAP sync config path: %w", err)
+	}
+
 	user, err := user.New(
 		ctx,
 		vault,
 		client,
 		bridge.reporter,
 		apiUser,
-		bridge.crashHandler,
-		bridge.vault.SyncWorkers(),
+		bridge.panicHandler,
 		bridge.vault.GetShowAllMail(),
+		bridge.vault.GetMaxSyncMemory(),
+		bridge,
+		bridge.serverManager,
+		bridge.serverManager,
+		&bridgeEventSubscription{b: bridge},
+		bridge.syncService,
+		bridge.observabilityService,
+		syncSettingsPath,
+		isNew,
+		bridge.notificationStore,
+		bridge.unleashService.GetFlagValue,
 	)
 	if err != nil {
 		return fmt.Errorf("failed to create user: %w", err)
 	}
 
-	// Connect the user's address(es) to gluon.
-	if err := bridge.addIMAPUser(ctx, user); err != nil {
-		return fmt.Errorf("failed to add IMAP user: %w", err)
-	}
-
 	// Handle events coming from the user before forwarding them to the bridge.
 	// For example, if the user's addresses change, we need to update them in gluon.
 	bridge.tasks.Once(func(ctx context.Context) {
 		async.RangeContext(ctx, user.GetEventCh(), func(event events.Event) {
-			logrus.WithFields(logrus.Fields{
+			logUser.WithFields(logrus.Fields{
 				"userID": apiUser.ID,
 				"event":  event,
 			}).Debug("Received user event")
 
-			if err := bridge.handleUserEvent(ctx, user, event); err != nil {
-				logrus.WithError(err).Error("Failed to handle user event")
-			} else {
+			bridge.handleUserEvent(ctx, user, event)
 			bridge.publish(event)
-			}
 		})
 	})
 
@@ -495,7 +575,7 @@ func (bridge *Bridge) addUserWithVault(
 	// As such, if we find this ID in the context, we should use it to update our user agent.
 	client.AddPreRequestHook(func(_ *resty.Client, r *resty.Request) error {
 		if imapID, ok := imap.GetIMAPIDFromContext(r.Context()); ok {
-			bridge.identifier.SetClient(imapID.Name, imapID.Version)
+			bridge.setUserAgent(imapID.Name, imapID.Version)
 		}
 
 		return nil
@@ -504,8 +584,17 @@ func (bridge *Bridge) addUserWithVault(
 	// Finally, save the user in the bridge.
 	safe.Lock(func() {
 		bridge.users[apiUser.ID] = user
+		bridge.heartbeat.SetNumberConnectedAccounts(len(bridge.users))
 	}, bridge.usersLock)
 
+	// Set user plan if its of a higher rank.
+	bridge.heartbeat.SetUserPlan(user.GetUserPlanName())
+
+	// As we need at least one user to send heartbeat, try to send it.
+	bridge.heartbeat.start()
+
+	user.PublishEvent(ctx, events.UserLoadedCheckResync{UserID: user.ID()})
+
 	return nil
 }
 
@@ -516,48 +605,24 @@ func (bridge *Bridge) newVaultUser(
 	authUID, authRef string,
 	saltedKeyPass []byte,
 ) (*vault.User, bool, error) {
-	if !bridge.vault.HasUser(apiUser.ID) {
-		user, err := bridge.vault.AddUser(apiUser.ID, apiUser.Name, apiUser.Email, authUID, authRef, saltedKeyPass)
-		if err != nil {
-			return nil, false, fmt.Errorf("failed to add user to vault: %w", err)
-		}
-
-		return user, true, nil
-	}
-
-	user, err := bridge.vault.NewUser(apiUser.ID)
-	if err != nil {
-		return nil, false, err
-	}
-
-	if err := user.SetAuth(authUID, authRef); err != nil {
-		return nil, false, err
-	}
-
-	if err := user.SetKeyPass(saltedKeyPass); err != nil {
-		return nil, false, err
-	}
-
-	return user, false, nil
+	return bridge.vault.GetOrAddUser(apiUser.ID, apiUser.Name, apiUser.Email, authUID, authRef, saltedKeyPass)
 }
 
-// logout logs out the given user, optionally logging them out from the API too.
+// logoutUser logs out the given user, optionally logging them out from the API and deleting user related gluon data.
 func (bridge *Bridge) logoutUser(ctx context.Context, user *user.User, withAPI, withData bool) {
 	defer delete(bridge.users, user.ID())
 
-	logrus.WithFields(logrus.Fields{
+	logUser.WithFields(logrus.Fields{
 		"userID":   user.ID(),
 		"withAPI":  withAPI,
 		"withData": withData,
 	}).Debug("Logging out user")
 
-	if err := bridge.removeIMAPUser(ctx, user, withData); err != nil {
-		logrus.WithError(err).Error("Failed to remove IMAP user")
+	if err := user.Logout(ctx, withAPI, withData, bridge.unleashService.GetFlagValue(unleash.UserRemovalGluonDataCleanupDisabled)); err != nil {
+		logUser.WithError(err).Error("Failed to logout user")
 	}
 
-	if err := user.Logout(ctx, withAPI); err != nil {
-		logrus.WithError(err).Error("Failed to logout user")
-	}
+	bridge.heartbeat.SetNumberConnectedAccounts(len(bridge.users) - 1)
 
 	user.Close()
 }

internal/bridge/user_event_test.go

@@ -1,4 +1,4 @@
-// Copyright (c) 2023 Proton AG
+// Copyright (c) 2025 Proton AG
 //
 // This file is part of Proton Mail Bridge.
 //
@@ -20,18 +20,24 @@ package bridge_test
 import (
 	"context"
 	"fmt"
+	"net"
 	"net/http"
+	"net/mail"
 	"strings"
 	"sync/atomic"
 	"testing"
 	"time"
 
+	"github.com/ProtonMail/gluon/async"
+	"github.com/ProtonMail/gluon/rfc822"
 	"github.com/ProtonMail/go-proton-api"
 	"github.com/ProtonMail/go-proton-api/server"
+	"github.com/ProtonMail/gopenpgp/v2/crypto"
 	"github.com/ProtonMail/proton-bridge/v3/internal/bridge"
 	"github.com/ProtonMail/proton-bridge/v3/internal/constants"
 	"github.com/ProtonMail/proton-bridge/v3/internal/events"
 	"github.com/ProtonMail/proton-bridge/v3/internal/user"
+	"github.com/bradenaw/juniper/stream"
 	"github.com/bradenaw/juniper/xslices"
 	"github.com/emersion/go-imap"
 	"github.com/emersion/go-imap/client"
@@ -40,7 +46,85 @@ import (
 	"github.com/stretchr/testify/require"
 )
 
+func TestBridge_User_RefreshEvent(t *testing.T) {
+	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, storeKey []byte) {
+		// Create a user.
+		userID, addrID, err := s.CreateUser("user", password)
+		require.NoError(t, err)
+
+		labelID, err := s.CreateLabel(userID, "folder", "", proton.LabelTypeFolder)
+		require.NoError(t, err)
+
+		var messageIDs []string
+
+		// Create 10 messages for the user.
+		withClient(ctx, t, s, "user", password, func(ctx context.Context, c *proton.Client) {
+			messageIDs = createNumMessages(ctx, t, c, addrID, labelID, 10)
+		})
+
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
+			userLoginAndSync(ctx, t, bridge, "user", password)
+		})
+
+		// Remove a message
+		withClient(ctx, t, s, "user", password, func(ctx context.Context, c *proton.Client) {
+			require.NoError(t, c.DeleteMessage(ctx, messageIDs[0]))
+		})
+
+		require.NoError(t, s.RefreshUser(userID, proton.RefreshMail))
+
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
+			syncCh, closeCh := chToType[events.Event, events.SyncFinished](bridge.GetEvents(events.SyncFinished{}))
+
+			require.Equal(t, userID, (<-syncCh).UserID)
+			closeCh()
+
+			userContinueEventProcess(ctx, t, s, bridge)
+		})
+
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
+			withClient(ctx, t, s, "user", password, func(ctx context.Context, c *proton.Client) {
+				createNumMessages(ctx, t, c, addrID, labelID, 10)
+			})
+
+			userContinueEventProcess(ctx, t, s, bridge)
+		})
+	})
+}
+
 func TestBridge_User_BadMessage_BadEvent(t *testing.T) {
+	t.Run("Resync", test_badMessage_badEvent(func(t *testing.T, ctx context.Context, bridge *bridge.Bridge, badUserID string) {
+		// User feedback is resync
+		require.NoError(t, bridge.SendBadEventUserFeedback(ctx, badUserID, true))
+
+		// Wait for sync to finish
+		syncCh, closeCh := chToType[events.Event, events.SyncFinished](bridge.GetEvents(events.SyncFinished{}))
+		require.Equal(t, badUserID, (<-syncCh).UserID)
+		closeCh()
+	}))
+
+	t.Run("LogoutAndLogin", test_badMessage_badEvent(func(t *testing.T, ctx context.Context, bridge *bridge.Bridge, badUserID string) {
+		logoutCh, closeCh := chToType[events.Event, events.UserLoggedOut](bridge.GetEvents(events.UserLoggedOut{}))
+
+		// User feedback is logout
+		require.NoError(t, bridge.SendBadEventUserFeedback(ctx, badUserID, false))
+
+		require.Equal(t, badUserID, (<-logoutCh).UserID)
+		closeCh()
+
+		// The user will eventually be logged out due to the bad request errors.
+		require.Eventually(t, func() bool {
+			return len(bridge.GetUserIDs()) == 1 && len(getConnectedUserIDs(t, bridge)) == 0
+		}, 100*user.EventPeriod, user.EventPeriod)
+
+		// Login again
+		_, err := bridge.LoginFull(ctx, "user", password, nil, nil)
+		require.NoError(t, err)
+	}))
+}
+
+func test_badMessage_badEvent(userFeedback func(t *testing.T, ctx context.Context, bridge *bridge.Bridge, badUserID string)) func(t *testing.T) {
+	return func(t *testing.T) {
 		withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, storeKey []byte) {
 			// Create a user.
 			userID, addrID, err := s.CreateUser("user", password)
@@ -71,7 +155,7 @@ func TestBridge_User_BadMessage_BadEvent(t *testing.T) {
 						return 0, false
 					}
 
-				if xslices.Index(xslices.Map(messageIDs, func(messageID string) string {
+					if xslices.Index(xslices.Map(messageIDs[0:5], func(messageID string) string {
 						return "/mail/v4/messages/" + messageID
 					}), req.URL.Path) < 0 {
 						return 0, false
@@ -80,21 +164,20 @@ func TestBridge_User_BadMessage_BadEvent(t *testing.T) {
 					return http.StatusBadRequest, true
 				})
 
-			userReceiveBadErrorAndLogout(t, bridge, mocks)
+				badUserID := userReceivesBadError(t, bridge, mocks)
 
-			// Remove messages
+				// Remove messages, make response OK again
 				withClient(ctx, t, s, "user", password, func(ctx context.Context, c *proton.Client) {
-				require.NoError(t, c.DeleteMessage(ctx, messageIDs...))
+					require.NoError(t, c.DeleteMessage(ctx, messageIDs[0:5]...))
 				})
 				doBadRequest = false
 
-			// Login again
-			_, err := bridge.LoginFull(ctx, "user", password, nil, nil)
-			require.NoError(t, err)
+				userFeedback(t, ctx, bridge, badUserID)
 
 				userContinueEventProcess(ctx, t, s, bridge)
 			})
 		})
+	}
 }
 
 func TestBridge_User_BadMessage_NoBadEvent(t *testing.T) {
@@ -108,17 +191,18 @@ func TestBridge_User_BadMessage_NoBadEvent(t *testing.T) {
 			createNumMessages(ctx, t, c, addrID, proton.InboxLabel, 10)
 		})
 
-		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, mocks *bridge.Mocks) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
 			userLoginAndSync(ctx, t, bridge, "user", password)
 
 			var messageIDs []string
 
+			// Create 10 more messages for the user, generating events.
+			withClient(ctx, t, s, "user", password, func(ctx context.Context, c *proton.Client) {
+				messageIDs = createNumMessages(ctx, t, c, addrID, proton.InboxLabel, 10)
+			})
+
 			// If bridge attempts to sync the new messages, it should get a BadRequest error.
 			s.AddStatusHook(func(req *http.Request) (int, bool) {
-				if len(messageIDs) < 3 {
-					return 0, false
-				}
-
 				if strings.Contains(req.URL.Path, "/mail/v4/messages/"+messageIDs[2]) {
 					return http.StatusUnprocessableEntity, true
 				}
@@ -126,11 +210,6 @@ func TestBridge_User_BadMessage_NoBadEvent(t *testing.T) {
 				return 0, false
 			})
 
-			// Create 10 more messages for the user, generating events.
-			withClient(ctx, t, s, "user", password, func(ctx context.Context, c *proton.Client) {
-				messageIDs = createNumMessages(ctx, t, c, addrID, proton.InboxLabel, 10)
-			})
-
 			// Remove messages
 			withClient(ctx, t, s, "user", password, func(ctx context.Context, c *proton.Client) {
 				require.NoError(t, c.DeleteMessage(ctx, messageIDs...))
@@ -249,6 +328,24 @@ func TestBridge_User_AddressEvents_NoBadEvent(t *testing.T) {
 	})
 }
 
+func TestBridge_User_AddressEventUpdatedForAddressThatDoesNotExist_NoBadEvent(t *testing.T) {
+	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, storeKey []byte) {
+		// Create a user.
+		userID, _, err := s.CreateUser("user", password)
+		require.NoError(t, err)
+
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
+			userLoginAndSync(ctx, t, bridge, "user", password)
+		})
+
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
+			_, err := s.CreateAddressAsUpdate(userID, "another@pm.me", password)
+			require.NoError(t, err)
+			userContinueEventProcess(ctx, t, s, bridge)
+		})
+	})
+}
+
 func TestBridge_User_Network_NoBadEvents(t *testing.T) {
 	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, storeKey []byte) {
 		retVal := int32(0)
@@ -271,7 +368,7 @@ func TestBridge_User_Network_NoBadEvents(t *testing.T) {
 		_, addrID, err := s.CreateUser("user", password)
 		require.NoError(t, err)
 
-		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, mocks *bridge.Mocks) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
 			userLoginAndSync(ctx, t, bridge, "user", password)
 
 			// Create 10 more messages for the user, generating events.
@@ -295,6 +392,453 @@ func TestBridge_User_Network_NoBadEvents(t *testing.T) {
 	})
 }
 
+func TestBridge_User_DropConn_NoBadEvent(t *testing.T) {
+	l, err := net.Listen("tcp", "127.0.0.1:0")
+	require.NoError(t, err)
+
+	dropListener := proton.NewListener(l, proton.NewDropConn)
+	defer func() { _ = dropListener.Close() }()
+
+	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, storeKey []byte) {
+		// Create a user.
+		_, addrID, err := s.CreateUser("user", password)
+		require.NoError(t, err)
+
+		// Create 10 messages for the user.
+		withClient(ctx, t, s, "user", password, func(ctx context.Context, c *proton.Client) {
+			createNumMessages(ctx, t, c, addrID, proton.InboxLabel, 10)
+		})
+
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, mocks *bridge.Mocks) {
+			var count int32
+			// The first 10 times bridge attempts to sync any of the messages, drop the connection.
+			s.AddStatusHook(func(req *http.Request) (int, bool) {
+				if strings.Contains(req.URL.Path, "/mail/v4/messages") {
+					if atomic.AddInt32(&count, 1) < 10 {
+						dropListener.DropAll()
+					}
+				}
+
+				return 0, false
+			})
+			userLoginAndSync(ctx, t, bridge, "user", password)
+
+			mocks.Reporter.EXPECT().ReportMessageWithContext(gomock.Any(), gomock.Any()).AnyTimes()
+
+			// Create 10 more messages for the user, generating events.
+			withClient(ctx, t, s, "user", password, func(ctx context.Context, c *proton.Client) {
+				createNumMessages(ctx, t, c, addrID, proton.InboxLabel, 10)
+			})
+
+			info, err := bridge.QueryUserInfo("user")
+			require.NoError(t, err)
+
+			cli, err := eventuallyDial(fmt.Sprintf("%v:%v", constants.Host, bridge.GetIMAPPort()))
+			require.NoError(t, err)
+			require.NoError(t, cli.Login(info.Addresses[0], string(info.BridgePass)))
+			defer func() { _ = cli.Logout() }()
+
+			// The IMAP client will eventually see 20 messages.
+			require.Eventually(t, func() bool {
+				status, err := cli.Status("INBOX", []imap.StatusItem{imap.StatusMessages})
+				return err == nil && status.Messages == 20
+			}, 10*time.Second, 100*time.Millisecond)
+		})
+	}, server.WithListener(dropListener))
+}
+
+func TestBridge_User_UpdateDraft(t *testing.T) {
+	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, storeKey []byte) {
+		// Create a bridge user.
+		_, _, err := s.CreateUser("user", password)
+		require.NoError(t, err)
+
+		// Initially sync the user.
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
+			userLoginAndSync(ctx, t, bridge, "user", password)
+		})
+
+		withClient(ctx, t, s, "user", password, func(ctx context.Context, c *proton.Client) {
+			user, err := c.GetUser(ctx)
+			require.NoError(t, err)
+
+			addrs, err := c.GetAddresses(ctx)
+			require.NoError(t, err)
+
+			salts, err := c.GetSalts(ctx)
+			require.NoError(t, err)
+
+			keyPass, err := salts.SaltForKey(password, user.Keys.Primary().ID)
+			require.NoError(t, err)
+
+			_, addrKRs, err := proton.Unlock(user, addrs, keyPass, async.NoopPanicHandler{})
+			require.NoError(t, err)
+
+			// Create a draft (generating a "create draft message" event).
+			draft, err := c.CreateDraft(ctx, addrKRs[addrs[0].ID], proton.CreateDraftReq{
+				Message: proton.DraftTemplate{
+					Subject:  "subject",
+					Sender:   &mail.Address{Name: "sender", Address: addrs[0].Email},
+					Body:     "body",
+					MIMEType: rfc822.TextPlain,
+				},
+			})
+			require.NoError(t, err)
+			require.Empty(t, draft.ReplyTos)
+
+			// Process those events
+			withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
+				userContinueEventProcess(ctx, t, s, bridge)
+			})
+
+			// Update the draft (generating an "update draft message" event).
+			draft2, err := c.UpdateDraft(ctx, draft.ID, addrKRs[addrs[0].ID], proton.UpdateDraftReq{
+				Message: proton.DraftTemplate{
+					Subject:  "subject 2",
+					Sender:   &mail.Address{Name: "sender", Address: addrs[0].Email},
+					Body:     "body 2",
+					MIMEType: rfc822.TextPlain,
+				},
+			})
+			require.NoError(t, err)
+			require.Empty(t, draft2.ReplyTos)
+		})
+	})
+}
+
+func TestBridge_User_UpdateDraftAndCreateOtherMessage(t *testing.T) {
+	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, storeKey []byte) {
+		// Create a bridge user.
+		_, _, err := s.CreateUser("user", password)
+		require.NoError(t, err)
+
+		// Initially sync the user.
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
+			userLoginAndSync(ctx, t, bridge, "user", password)
+		})
+
+		withClient(ctx, t, s, "user", password, func(ctx context.Context, c *proton.Client) {
+			user, err := c.GetUser(ctx)
+			require.NoError(t, err)
+
+			addrs, err := c.GetAddresses(ctx)
+			require.NoError(t, err)
+
+			salts, err := c.GetSalts(ctx)
+			require.NoError(t, err)
+
+			keyPass, err := salts.SaltForKey(password, user.Keys.Primary().ID)
+			require.NoError(t, err)
+
+			_, addrKRs, err := proton.Unlock(user, addrs, keyPass, async.NoopPanicHandler{})
+			require.NoError(t, err)
+
+			// Create a draft (generating a "create draft message" event).
+			draft, err := c.CreateDraft(ctx, addrKRs[addrs[0].ID], proton.CreateDraftReq{
+				Message: proton.DraftTemplate{
+					Subject:  "subject",
+					Sender:   &mail.Address{Name: "sender", Address: addrs[0].Email},
+					Body:     "body",
+					MIMEType: rfc822.TextPlain,
+				},
+			})
+			require.NoError(t, err)
+
+			// Process those events
+			withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
+				userContinueEventProcess(ctx, t, s, bridge)
+			})
+
+			// Update the draft (generating an "update draft message" event).
+			require.NoError(t, getErr(c.UpdateDraft(ctx, draft.ID, addrKRs[addrs[0].ID], proton.UpdateDraftReq{
+				Message: proton.DraftTemplate{
+					Subject:  "subject 2",
+					Sender:   &mail.Address{Name: "sender", Address: addrs[0].Email},
+					Body:     "body 2",
+					MIMEType: rfc822.TextPlain,
+				},
+			})))
+
+			// Import a message (generating a "create message" event).
+			str, err := c.ImportMessages(ctx, addrKRs[addrs[0].ID], 1, 1, proton.ImportReq{
+				Metadata: proton.ImportMetadata{
+					AddressID: addrs[0].ID,
+					Flags:     proton.MessageFlagReceived,
+				},
+				Message: []byte("From: someone@example.com\r\nTo: blabla@example.com\r\n\r\nhello"),
+			})
+			require.NoError(t, err)
+
+			res, err := stream.Collect(ctx, str)
+			require.NoError(t, err)
+
+			// Process those events.
+			withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
+				userContinueEventProcess(ctx, t, s, bridge)
+			})
+
+			// Update the imported message (generating an "update message" event).
+			require.NoError(t, c.MarkMessagesUnread(ctx, res[0].MessageID))
+
+			// Process those events.
+			withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
+				userContinueEventProcess(ctx, t, s, bridge)
+			})
+		})
+	})
+}
+
+func TestBridge_User_SendDraftRemoveDraftFlag(t *testing.T) {
+	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, storeKey []byte) {
+		// Create a bridge user.
+		_, _, err := s.CreateUser("user", password)
+		require.NoError(t, err)
+
+		// Initially sync the user.
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
+			userLoginAndSync(ctx, t, bridge, "user", password)
+		})
+
+		withClient(ctx, t, s, "user", password, func(ctx context.Context, c *proton.Client) {
+			user, err := c.GetUser(ctx)
+			require.NoError(t, err)
+
+			addrs, err := c.GetAddresses(ctx)
+			require.NoError(t, err)
+
+			salts, err := c.GetSalts(ctx)
+			require.NoError(t, err)
+
+			keyPass, err := salts.SaltForKey(password, user.Keys.Primary().ID)
+			require.NoError(t, err)
+
+			_, addrKRs, err := proton.Unlock(user, addrs, keyPass, async.NoopPanicHandler{})
+			require.NoError(t, err)
+
+			// Create a draft (generating a "create draft message" event).
+			draft, err := c.CreateDraft(ctx, addrKRs[addrs[0].ID], proton.CreateDraftReq{
+				Message: proton.DraftTemplate{
+					Subject:  "subject",
+					ToList:   []*mail.Address{{Address: addrs[0].Email}},
+					Sender:   &mail.Address{Name: "sender", Address: addrs[0].Email},
+					Body:     "body",
+					MIMEType: rfc822.TextPlain,
+				},
+			})
+			require.NoError(t, err)
+
+			// Process those events
+			withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
+				userContinueEventProcess(ctx, t, s, bridge)
+
+				info, err := bridge.QueryUserInfo("user")
+				require.NoError(t, err)
+
+				cli, err := eventuallyDial(fmt.Sprintf("%v:%v", constants.Host, bridge.GetIMAPPort()))
+				require.NoError(t, err)
+				require.NoError(t, cli.Login(info.Addresses[0], string(info.BridgePass)))
+				defer func() { _ = cli.Logout() }()
+
+				messages, err := clientFetch(cli, "Drafts")
+				require.NoError(t, err)
+				require.Len(t, messages, 1)
+				require.Contains(t, messages[0].Flags, imap.DraftFlag)
+			})
+
+			// Send the draft (generating an "update message" event).
+			{
+				pubKeys, recType, err := c.GetPublicKeys(ctx, addrs[0].Email)
+				require.NoError(t, err)
+				require.Equal(t, recType, proton.RecipientTypeInternal)
+
+				var req proton.SendDraftReq
+
+				require.NoError(t, req.AddTextPackage(addrKRs[addrs[0].ID], "body", rfc822.TextPlain, map[string]proton.SendPreferences{
+					addrs[0].Email: {
+						Encrypt:          true,
+						PubKey:           must(crypto.NewKeyRing(must(crypto.NewKeyFromArmored(pubKeys[0].PublicKey)))),
+						SignatureType:    proton.DetachedSignature,
+						EncryptionScheme: proton.InternalScheme,
+						MIMEType:         rfc822.TextPlain,
+					},
+				}, nil))
+
+				require.NoError(t, getErr(c.SendDraft(ctx, draft.ID, req)))
+			}
+
+			// Process those events; the draft will move to the sent folder and lose the draft flag.
+			withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
+				userContinueEventProcess(ctx, t, s, bridge)
+
+				info, err := bridge.QueryUserInfo("user")
+				require.NoError(t, err)
+
+				cli, err := eventuallyDial(fmt.Sprintf("%v:%v", constants.Host, bridge.GetIMAPPort()))
+				require.NoError(t, err)
+				require.NoError(t, cli.Login(info.Addresses[0], string(info.BridgePass)))
+				defer func() { _ = cli.Logout() }()
+
+				messages, err := clientFetch(cli, "Sent")
+				require.NoError(t, err)
+				require.Len(t, messages, 1)
+				require.NotContains(t, messages[0].Flags, imap.DraftFlag)
+			})
+		})
+	})
+}
+
+func TestBridge_User_DisableEnableAddress(t *testing.T) {
+	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, storeKey []byte) {
+		// Create a user.
+		userID, _, err := s.CreateUser("user", password)
+		require.NoError(t, err)
+
+		// Create an additional address for the user.
+		aliasID, err := s.CreateAddress(userID, "alias@"+s.GetDomain(), password)
+		require.NoError(t, err)
+
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
+			require.NoError(t, getErr(bridge.LoginFull(ctx, "user", password, nil, nil)))
+
+			// Initially we should list the address.
+			info, err := bridge.QueryUserInfo("user")
+			require.NoError(t, err)
+			require.Contains(t, info.Addresses, "alias@"+s.GetDomain())
+		})
+
+		// Disable the address.
+		withClient(ctx, t, s, "user", password, func(ctx context.Context, c *proton.Client) {
+			require.NoError(t, c.DisableAddress(ctx, aliasID))
+		})
+
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
+			// Eventually we shouldn't list the address.
+			require.Eventually(t, func() bool {
+				info, err := bridge.QueryUserInfo("user")
+				require.NoError(t, err)
+
+				return xslices.Index(info.Addresses, "alias@"+s.GetDomain()) < 0
+			}, 5*time.Second, 100*time.Millisecond)
+		})
+
+		// Enable the address.
+		withClient(ctx, t, s, "user", password, func(ctx context.Context, c *proton.Client) {
+			require.NoError(t, c.EnableAddress(ctx, aliasID))
+		})
+
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
+			// Eventually we should list the address.
+			require.Eventually(t, func() bool {
+				info, err := bridge.QueryUserInfo("user")
+				require.NoError(t, err)
+
+				return xslices.Index(info.Addresses, "alias@"+s.GetDomain()) >= 0
+			}, 5*time.Second, 100*time.Millisecond)
+		})
+	})
+}
+
+func TestBridge_User_CreateDisabledAddress(t *testing.T) {
+	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, storeKey []byte) {
+		// Create a user.
+		userID, _, err := s.CreateUser("user", password)
+		require.NoError(t, err)
+
+		// Create an additional address for the user.
+		aliasID, err := s.CreateAddress(userID, "alias@"+s.GetDomain(), password)
+		require.NoError(t, err)
+
+		// Immediately disable the address.
+		withClient(ctx, t, s, "user", password, func(ctx context.Context, c *proton.Client) {
+			require.NoError(t, c.DisableAddress(ctx, aliasID))
+		})
+
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
+			require.NoError(t, getErr(bridge.LoginFull(ctx, "user", password, nil, nil)))
+
+			// Initially we shouldn't list the address.
+			info, err := bridge.QueryUserInfo("user")
+			require.NoError(t, err)
+			require.NotContains(t, info.Addresses, "alias@"+s.GetDomain())
+		})
+	})
+}
+
+func TestBridge_User_HandleParentLabelRename(t *testing.T) {
+	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, storeKey []byte) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
+			require.NoError(t, getErr(bridge.LoginFull(ctx, username, password, nil, nil)))
+
+			info, err := bridge.QueryUserInfo(username)
+			require.NoError(t, err)
+
+			cli, err := eventuallyDial(fmt.Sprintf("%v:%v", constants.Host, bridge.GetIMAPPort()))
+			require.NoError(t, err)
+			require.NoError(t, cli.Login(info.Addresses[0], string(info.BridgePass)))
+			defer func() { _ = cli.Logout() }()
+
+			withClient(ctx, t, s, username, password, func(ctx context.Context, c *proton.Client) {
+				parentName := uuid.NewString()
+				childName := uuid.NewString()
+
+				// Create a folder.
+				parentLabel, err := c.CreateLabel(ctx, proton.CreateLabelReq{
+					Name:  parentName,
+					Type:  proton.LabelTypeFolder,
+					Color: "#f66",
+				})
+				require.NoError(t, err)
+
+				// Wait for the parent folder to be created.
+				require.Eventually(t, func() bool {
+					return xslices.IndexFunc(clientList(cli), func(mailbox *imap.MailboxInfo) bool {
+						return mailbox.Name == fmt.Sprintf("Folders/%v", parentName)
+					}) >= 0
+				}, 100*user.EventPeriod, user.EventPeriod)
+
+				// Create a subfolder.
+				childLabel, err := c.CreateLabel(ctx, proton.CreateLabelReq{
+					Name:     childName,
+					Type:     proton.LabelTypeFolder,
+					Color:    "#f66",
+					ParentID: parentLabel.ID,
+				})
+				require.NoError(t, err)
+				require.Equal(t, parentLabel.ID, childLabel.ParentID)
+
+				// Wait for the parent folder to be created.
+				require.Eventually(t, func() bool {
+					return xslices.IndexFunc(clientList(cli), func(mailbox *imap.MailboxInfo) bool {
+						return mailbox.Name == fmt.Sprintf("Folders/%v/%v", parentName, childName)
+					}) >= 0
+				}, 100*user.EventPeriod, user.EventPeriod)
+
+				newParentName := uuid.NewString()
+
+				// Rename the parent folder.
+				require.NoError(t, getErr(c.UpdateLabel(ctx, parentLabel.ID, proton.UpdateLabelReq{
+					Color: "#f66",
+					Name:  newParentName,
+				})))
+
+				// Wait for the parent folder to be renamed.
+				require.Eventually(t, func() bool {
+					return xslices.IndexFunc(clientList(cli), func(mailbox *imap.MailboxInfo) bool {
+						return mailbox.Name == fmt.Sprintf("Folders/%v", newParentName)
+					}) >= 0
+				}, 100*user.EventPeriod, user.EventPeriod)
+
+				// Wait for the child folder to be renamed.
+				require.Eventually(t, func() bool {
+					return xslices.IndexFunc(clientList(cli), func(mailbox *imap.MailboxInfo) bool {
+						return mailbox.Name == fmt.Sprintf("Folders/%v/%v", newParentName, childName)
+					}) >= 0
+				}, 100*user.EventPeriod, user.EventPeriod)
+			})
+		})
+	})
+}
+
 // userLoginAndSync logs in user and waits until user is fully synced.
 func userLoginAndSync(
 	ctx context.Context,
@@ -311,21 +855,24 @@ func userLoginAndSync(
 	require.Equal(t, userID, (<-syncCh).UserID)
 }
 
-func userReceiveBadErrorAndLogout(
+func userReceivesBadError(
 	t *testing.T,
 	bridge *bridge.Bridge,
 	mocks *bridge.Mocks,
-) {
+) (userID string) {
+	badEventCh, closeCh := bridge.GetEvents(events.UserBadEvent{})
+
 	// The user will continue to process events and will receive bad request errors.
 	mocks.Reporter.EXPECT().ReportMessageWithContext(gomock.Any(), gomock.Any()).MinTimes(1)
 
-	// The user will eventually be logged out due to the bad request errors.
-	require.Eventually(t, func() bool {
-		return len(bridge.GetUserIDs()) == 1 && len(getConnectedUserIDs(t, bridge)) == 0
-	}, 100*user.EventPeriod, user.EventPeriod)
+	badEvent, ok := (<-badEventCh).(events.UserBadEvent)
+	require.True(t, ok)
+
+	closeCh()
+
+	return badEvent.UserID
 }
 
-// userContinueEventProcess checks that user will continue to process events and will not receive any bad request errors.
 func userContinueEventProcess(
 	ctx context.Context,
 	t *testing.T,
@@ -335,10 +882,10 @@ func userContinueEventProcess(
 	info, err := bridge.QueryUserInfo("user")
 	require.NoError(t, err)
 
-	client, err := client.Dial(fmt.Sprintf("%v:%v", constants.Host, bridge.GetIMAPPort()))
+	cli, err := eventuallyDial(fmt.Sprintf("%v:%v", constants.Host, bridge.GetIMAPPort()))
 	require.NoError(t, err)
-	require.NoError(t, client.Login(info.Addresses[0], string(info.BridgePass)))
-	defer func() { _ = client.Logout() }()
+	require.NoError(t, cli.Login(info.Addresses[0], string(info.BridgePass)))
+	defer func() { _ = cli.Logout() }()
 
 	randomLabel := uuid.NewString()
 
@@ -353,8 +900,21 @@ func userContinueEventProcess(
 
 	// Wait for the label to be created.
 	require.Eventually(t, func() bool {
-		return xslices.IndexFunc(clientList(client), func(mailbox *imap.MailboxInfo) bool {
+		return xslices.IndexFunc(clientList(cli), func(mailbox *imap.MailboxInfo) bool {
 			return mailbox.Name == "Labels/"+randomLabel
 		}) >= 0
 	}, 100*user.EventPeriod, user.EventPeriod)
 }
+
+func eventuallyDial(addr string) (cli *client.Client, err error) {
+	var sleep = 1 * time.Second
+	for i := 0; i < 5; i++ {
+		cli, err := client.Dial(addr)
+		if err == nil {
+			return cli, nil
+		}
+		time.Sleep(sleep)
+		sleep *= 2
+	}
+	return nil, fmt.Errorf("after 5 attempts, last error: %s", err)
+}

internal/bridge/user_events.go

@@ -1,4 +1,4 @@
-// Copyright (c) 2023 Proton AG
+// Copyright (c) 2025 Proton AG
 //
 // This file is part of Proton Mail Bridge.
 //
@@ -19,115 +19,26 @@ package bridge
 
 import (
 	"context"
-	"fmt"
 
 	"github.com/ProtonMail/gluon/reporter"
+	"github.com/ProtonMail/proton-bridge/v3/internal"
 	"github.com/ProtonMail/proton-bridge/v3/internal/events"
 	"github.com/ProtonMail/proton-bridge/v3/internal/safe"
 	"github.com/ProtonMail/proton-bridge/v3/internal/user"
-	"github.com/ProtonMail/proton-bridge/v3/internal/vault"
 	"github.com/sirupsen/logrus"
 )
 
-func (bridge *Bridge) handleUserEvent(ctx context.Context, user *user.User, event events.Event) error {
+func (bridge *Bridge) handleUserEvent(ctx context.Context, user *user.User, event events.Event) {
 	switch event := event.(type) {
-	case events.UserAddressCreated:
-		if err := bridge.handleUserAddressCreated(ctx, user, event); err != nil {
-			return fmt.Errorf("failed to handle user address created event: %w", err)
-		}
-
-	case events.UserAddressUpdated:
-		if err := bridge.handleUserAddressUpdated(ctx, user, event); err != nil {
-			return fmt.Errorf("failed to handle user address updated event: %w", err)
-		}
-
-	case events.UserAddressDeleted:
-		if err := bridge.handleUserAddressDeleted(ctx, user, event); err != nil {
-			return fmt.Errorf("failed to handle user address deleted event: %w", err)
-		}
-
-	case events.UserRefreshed:
-		if err := bridge.handleUserRefreshed(ctx, user); err != nil {
-			return fmt.Errorf("failed to handle user refreshed event: %w", err)
-		}
-
 	case events.UserDeauth:
 		bridge.handleUserDeauth(ctx, user)
 
 	case events.UserBadEvent:
-		bridge.handleUserBadEvent(ctx, user, event.Error)
+		bridge.handleUserBadEvent(ctx, user, event)
+
+	case events.UserLoadedCheckResync:
+		user.VerifyResyncAndExecute()
 	}
-
-	return nil
-}
-
-func (bridge *Bridge) handleUserAddressCreated(ctx context.Context, user *user.User, event events.UserAddressCreated) error {
-	if user.GetAddressMode() == vault.SplitMode {
-		if bridge.imapServer == nil {
-			return fmt.Errorf("no imap server instance running")
-		}
-
-		gluonID, err := bridge.imapServer.AddUser(ctx, user.NewIMAPConnector(event.AddressID), user.GluonKey())
-		if err != nil {
-			return fmt.Errorf("failed to add user to IMAP server: %w", err)
-		}
-
-		if err := user.SetGluonID(event.AddressID, gluonID); err != nil {
-			return fmt.Errorf("failed to set gluon ID: %w", err)
-		}
-	}
-
-	return nil
-}
-
-// GODT-1948: Handle addresses that have been disabled!
-func (bridge *Bridge) handleUserAddressUpdated(_ context.Context, user *user.User, _ events.UserAddressUpdated) error {
-	switch user.GetAddressMode() {
-	case vault.CombinedMode:
-		return fmt.Errorf("not implemented")
-
-	case vault.SplitMode:
-		return fmt.Errorf("not implemented")
-	}
-
-	return nil
-}
-
-func (bridge *Bridge) handleUserAddressDeleted(ctx context.Context, user *user.User, event events.UserAddressDeleted) error {
-	if user.GetAddressMode() == vault.SplitMode {
-		if bridge.imapServer == nil {
-			return fmt.Errorf("no imap server instance running")
-		}
-
-		gluonID, ok := user.GetGluonID(event.AddressID)
-		if !ok {
-			return fmt.Errorf("gluon ID not found for address %s", event.AddressID)
-		}
-
-		if err := bridge.imapServer.RemoveUser(ctx, gluonID, true); err != nil {
-			return fmt.Errorf("failed to remove user from IMAP server: %w", err)
-		}
-
-		if err := user.RemoveGluonID(event.AddressID, gluonID); err != nil {
-			return fmt.Errorf("failed to remove gluon ID for address: %w", err)
-		}
-	}
-
-	return nil
-}
-
-func (bridge *Bridge) handleUserRefreshed(ctx context.Context, user *user.User) error {
-	return safe.RLockRet(func() error {
-		if err := bridge.removeIMAPUser(ctx, user, true); err != nil {
-			return fmt.Errorf("failed to remove IMAP user: %w", err)
-		}
-
-		if err := bridge.addIMAPUser(ctx, user); err != nil {
-			return fmt.Errorf("failed to add IMAP user: %w", err)
-		}
-
-		return nil
-	}, bridge.usersLock)
 }
 
 func (bridge *Bridge) handleUserDeauth(ctx context.Context, user *user.User) {
@@ -136,14 +47,19 @@ func (bridge *Bridge) handleUserDeauth(ctx context.Context, user *user.User) {
 	}, bridge.usersLock)
 }
 
-func (bridge *Bridge) handleUserBadEvent(ctx context.Context, user *user.User, err error) {
-	safe.Lock(func() {
+func (bridge *Bridge) handleUserBadEvent(ctx context.Context, user *user.User, event events.UserBadEvent) {
+	safe.RLock(func() {
 		if rerr := bridge.reporter.ReportMessageWithContext("Failed to handle event", reporter.Context{
-			"error": err,
+			"user_id":      user.ID(),
+			"old_event_id": event.OldEventID,
+			"new_event_id": event.NewEventID,
+			"event_info":   event.EventInfo,
+			"error":        event.Error,
+			"error_type":   internal.ErrCauseType(event.Error),
 		}); rerr != nil {
-			logrus.WithError(rerr).Error("Failed to report failed event handling")
+			logrus.WithField("pkg", "bridge/event").WithError(rerr).Error("Failed to report failed event handling")
 		}
 
-		bridge.logoutUser(ctx, user, true, false)
+		user.OnBadEvent(ctx)
 	}, bridge.usersLock)
 }

internal/bridge/user_test.go

@@ -1,4 +1,4 @@
-// Copyright (c) 2023 Proton AG
+// Copyright (c) 2025 Proton AG
 //
 // This file is part of Proton Mail Bridge.
 //
@@ -20,27 +20,27 @@ package bridge_test
 import (
 	"context"
 	"fmt"
+	"net"
+	"net/http"
 	"testing"
 	"time"
 
 	"github.com/ProtonMail/go-proton-api"
 	"github.com/ProtonMail/go-proton-api/server"
 	"github.com/ProtonMail/proton-bridge/v3/internal/bridge"
-	mocksPkg "github.com/ProtonMail/proton-bridge/v3/internal/bridge/mocks"
 	"github.com/ProtonMail/proton-bridge/v3/internal/events"
 	"github.com/ProtonMail/proton-bridge/v3/internal/vault"
-	"github.com/golang/mock/gomock"
 	"github.com/stretchr/testify/require"
 )
 
 func TestBridge_WithoutUsers(t *testing.T) {
 	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, storeKey []byte) {
-		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, mocks *bridge.Mocks) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
 			require.Empty(t, bridge.GetUserIDs())
 			require.Empty(t, getConnectedUserIDs(t, bridge))
 		})
 
-		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, mocks *bridge.Mocks) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
 			require.Empty(t, bridge.GetUserIDs())
 			require.Empty(t, getConnectedUserIDs(t, bridge))
 		})
@@ -49,7 +49,7 @@ func TestBridge_WithoutUsers(t *testing.T) {
 
 func TestBridge_Login(t *testing.T) {
 	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, storeKey []byte) {
-		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, mocks *bridge.Mocks) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
 			// Login the user.
 			userID, err := bridge.LoginFull(ctx, username, password, nil, nil)
 			require.NoError(t, err)
@@ -61,9 +61,53 @@ func TestBridge_Login(t *testing.T) {
 	})
 }
 
+func TestBridge_Login_DropConn(t *testing.T) {
+	l, err := net.Listen("tcp", "127.0.0.1:0")
+	require.NoError(t, err)
+
+	dropListener := proton.NewListener(l, proton.NewDropConn)
+	defer func() { _ = dropListener.Close() }()
+
+	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, storeKey []byte) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
+			// Login the user.
+			userID, err := bridge.LoginFull(ctx, username, password, nil, nil)
+			require.NoError(t, err)
+
+			// The user is now connected.
+			require.Equal(t, []string{userID}, bridge.GetUserIDs())
+			require.Equal(t, []string{userID}, getConnectedUserIDs(t, bridge))
+		})
+
+		// Whether to allow the user to be created.
+		var allowUser bool
+
+		s.AddStatusHook(func(req *http.Request) (int, bool) {
+			// Drop any request to the users endpoint.
+			if !allowUser && req.URL.Path == "/core/v4/users" {
+				dropListener.DropAll()
+			}
+
+			// After the ping request, allow the user to be created.
+			if req.URL.Path == "/tests/ping" {
+				allowUser = true
+			}
+
+			return 0, false
+		})
+
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
+			// The user is eventually connected.
+			require.Eventually(t, func() bool {
+				return len(bridge.GetUserIDs()) == 1 && len(getConnectedUserIDs(t, bridge)) == 1
+			}, 5*time.Second, 100*time.Millisecond)
+		})
+	}, server.WithListener(dropListener))
+}
+
 func TestBridge_LoginTwice(t *testing.T) {
 	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, storeKey []byte) {
-		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, mocks *bridge.Mocks) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
 			// Login the user.
 			userID, err := bridge.LoginFull(ctx, username, password, nil, nil)
 			require.NoError(t, err)
@@ -81,7 +125,7 @@ func TestBridge_LoginTwice(t *testing.T) {
 
 func TestBridge_LoginLogoutLogin(t *testing.T) {
 	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, storeKey []byte) {
-		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, mocks *bridge.Mocks) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
 			// Login the user.
 			userID := must(bridge.LoginFull(ctx, username, password, nil, nil))
 
@@ -109,7 +153,7 @@ func TestBridge_LoginLogoutLogin(t *testing.T) {
 
 func TestBridge_LoginDeleteLogin(t *testing.T) {
 	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, storeKey []byte) {
-		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, mocks *bridge.Mocks) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
 			// Login the user.
 			userID := must(bridge.LoginFull(ctx, username, password, nil, nil))
 
@@ -137,7 +181,7 @@ func TestBridge_LoginDeleteLogin(t *testing.T) {
 
 func TestBridge_LoginDeauthLogin(t *testing.T) {
 	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, storeKey []byte) {
-		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, mocks *bridge.Mocks) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
 			// Login the user.
 			userID := must(bridge.LoginFull(ctx, username, password, nil, nil))
 
@@ -171,7 +215,7 @@ func TestBridge_LoginDeauthRestartLogin(t *testing.T) {
 	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, storeKey []byte) {
 		var userID string
 
-		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, mocks *bridge.Mocks) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
 			// Login the user.
 			userID = must(bridge.LoginFull(ctx, username, password, nil, nil))
 
@@ -191,7 +235,7 @@ func TestBridge_LoginDeauthRestartLogin(t *testing.T) {
 			require.IsType(t, events.UserDeauth{}, <-eventCh)
 		})
 
-		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, mocks *bridge.Mocks) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
 			// The user should be disconnected at startup.
 			require.Equal(t, []string{userID}, bridge.GetUserIDs())
 			require.Empty(t, getConnectedUserIDs(t, bridge))
@@ -213,7 +257,7 @@ func TestBridge_LoginExpireLogin(t *testing.T) {
 	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, storeKey []byte) {
 		s.SetAuthLife(authLife)
 
-		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, mocks *bridge.Mocks) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
 			// Login the user. Its auth will only be valid for a short time.
 			userID := must(bridge.LoginFull(ctx, username, password, nil, nil))
 
@@ -231,7 +275,7 @@ func TestBridge_FailToLoad(t *testing.T) {
 		var userID string
 
 		// Login the user.
-		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, mocks *bridge.Mocks) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
 			userID = must(bridge.LoginFull(ctx, username, password, nil, nil))
 		})
 
@@ -239,7 +283,7 @@ func TestBridge_FailToLoad(t *testing.T) {
 		require.NoError(t, s.RevokeUser(userID))
 
 		// When bridge starts, the user will not be logged in.
-		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, mocks *bridge.Mocks) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
 			require.Equal(t, []string{userID}, bridge.GetUserIDs())
 			require.Empty(t, getConnectedUserIDs(t, bridge))
 		})
@@ -251,7 +295,7 @@ func TestBridge_LoadWithoutInternet(t *testing.T) {
 		var userID string
 
 		// Login the user.
-		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, mocks *bridge.Mocks) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
 			userID = must(bridge.LoginFull(ctx, username, password, nil, nil))
 		})
 
@@ -259,7 +303,7 @@ func TestBridge_LoadWithoutInternet(t *testing.T) {
 		netCtl.Disable()
 
 		// Start bridge without internet.
-		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, mocks *bridge.Mocks) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
 			// Initially, users are not connected.
 			require.Equal(t, []string{userID}, bridge.GetUserIDs())
 			require.Empty(t, getConnectedUserIDs(t, bridge))
@@ -281,11 +325,11 @@ func TestBridge_LoginRestart(t *testing.T) {
 	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, storeKey []byte) {
 		var userID string
 
-		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, mocks *bridge.Mocks) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
 			userID = must(bridge.LoginFull(ctx, username, password, nil, nil))
 		})
 
-		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, mocks *bridge.Mocks) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
 			require.Equal(t, []string{userID}, bridge.GetUserIDs())
 			require.Equal(t, []string{userID}, getConnectedUserIDs(t, bridge))
 		})
@@ -296,7 +340,7 @@ func TestBridge_LoginLogoutRestart(t *testing.T) {
 	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, storeKey []byte) {
 		var userID string
 
-		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, mocks *bridge.Mocks) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
 			// Login the user.
 			userID = must(bridge.LoginFull(ctx, username, password, nil, nil))
 
@@ -304,7 +348,7 @@ func TestBridge_LoginLogoutRestart(t *testing.T) {
 			require.NoError(t, bridge.LogoutUser(ctx, userID))
 		})
 
-		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, mocks *bridge.Mocks) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
 			// The user is still disconnected.
 			require.Equal(t, []string{userID}, bridge.GetUserIDs())
 			require.Empty(t, getConnectedUserIDs(t, bridge))
@@ -316,7 +360,7 @@ func TestBridge_LoginDeleteRestart(t *testing.T) {
 	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, storeKey []byte) {
 		var userID string
 
-		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, mocks *bridge.Mocks) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
 			// Login the user.
 			userID = must(bridge.LoginFull(ctx, username, password, nil, nil))
 
@@ -324,7 +368,7 @@ func TestBridge_LoginDeleteRestart(t *testing.T) {
 			require.NoError(t, bridge.DeleteUser(ctx, userID))
 		})
 
-		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, mocks *bridge.Mocks) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
 			// The user is still gone.
 			require.Empty(t, bridge.GetUserIDs())
 			require.Empty(t, getConnectedUserIDs(t, bridge))
@@ -340,7 +384,7 @@ func TestBridge_FailLoginRecover(t *testing.T) {
 
 				// Log the user in, wait for it to sync, then log it out.
 				// (We don't want to count message sync data in the test.)
-				withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, mocks *bridge.Mocks) {
+				withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
 					syncCh, done := chToType[events.Event, events.SyncFinished](bridge.GetEvents(events.SyncFinished{}))
 					defer done()
 
@@ -352,7 +396,7 @@ func TestBridge_FailLoginRecover(t *testing.T) {
 				var total uint64
 
 				// Now that the user is synced, we can measure exactly how much data is needed during login.
-				withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, mocks *bridge.Mocks) {
+				withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
 					total = countBytesRead(netCtl, func() {
 						must(bridge.LoginFull(ctx, username, password, nil, nil))
 					})
@@ -361,7 +405,7 @@ func TestBridge_FailLoginRecover(t *testing.T) {
 				})
 
 				// Now simulate failing to login.
-				withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, mocks *bridge.Mocks) {
+				withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
 					// Simulate a partial read.
 					netCtl.SetReadLimit(i * total / 10)
 
@@ -377,7 +421,7 @@ func TestBridge_FailLoginRecover(t *testing.T) {
 				netCtl.SetReadLimit(0)
 
 				// We should now be able to log the user in.
-				withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, mocks *bridge.Mocks) {
+				withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
 					require.NoError(t, getErr(bridge.LoginFull(ctx, username, password, nil, nil)))
 
 					// The user should be there, now connected.
@@ -397,7 +441,7 @@ func TestBridge_FailLoadRecover(t *testing.T) {
 
 				// Log the user in and wait for it to sync.
 				// (We don't want to count message sync data in the test.)
-				withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, mocks *bridge.Mocks) {
+				withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
 					syncCh, done := chToType[events.Event, events.SyncFinished](bridge.GetEvents(events.SyncFinished{}))
 					defer done()
 
@@ -407,7 +451,7 @@ func TestBridge_FailLoadRecover(t *testing.T) {
 
 				// See how much data it takes to load the user at startup.
 				total := countBytesRead(netCtl, func() {
-					withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, mocks *bridge.Mocks) {
+					withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(_ *bridge.Bridge, _ *bridge.Mocks) {
 						// ...
 					})
 				})
@@ -416,7 +460,7 @@ func TestBridge_FailLoadRecover(t *testing.T) {
 				netCtl.SetReadLimit(i * total / 10)
 
 				// We should fail to load the user; it should be listed but disconnected.
-				withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, mocks *bridge.Mocks) {
+				withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
 					require.Equal(t, []string{userID}, bridge.GetUserIDs())
 					require.Empty(t, getConnectedUserIDs(t, bridge))
 				})
@@ -425,7 +469,7 @@ func TestBridge_FailLoadRecover(t *testing.T) {
 				netCtl.SetReadLimit(0)
 
 				// We should now be able to load the user.
-				withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, mocks *bridge.Mocks) {
+				withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
 					require.Equal(t, []string{userID}, bridge.GetUserIDs())
 					require.Equal(t, []string{userID}, getConnectedUserIDs(t, bridge))
 				})
@@ -440,7 +484,7 @@ func TestBridge_BridgePass(t *testing.T) {
 
 		var pass []byte
 
-		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, mocks *bridge.Mocks) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
 			// Login the user.
 			userID = must(bridge.LoginFull(ctx, username, password, nil, nil))
 
@@ -457,7 +501,7 @@ func TestBridge_BridgePass(t *testing.T) {
 			require.Equal(t, pass, pass)
 		})
 
-		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, mocks *bridge.Mocks) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
 			// The bridge should load the user.
 			require.Equal(t, []string{userID}, bridge.GetUserIDs())
 			require.Equal(t, []string{userID}, getConnectedUserIDs(t, bridge))
@@ -470,7 +514,7 @@ func TestBridge_BridgePass(t *testing.T) {
 
 func TestBridge_AddressMode(t *testing.T) {
 	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, storeKey []byte) {
-		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, mocks *bridge.Mocks) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
 			// Login the user.
 			userID, err := bridge.LoginFull(ctx, username, password, nil, nil)
 			require.NoError(t, err)
@@ -508,7 +552,7 @@ func TestBridge_AddressMode(t *testing.T) {
 
 func TestBridge_LoginLogoutRepeated(t *testing.T) {
 	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, storeKey []byte) {
-		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, mocks *bridge.Mocks) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
 			for i := 0; i < 10; i++ {
 				// Log the user in.
 				userID := must(bridge.LoginFull(ctx, username, password, nil, nil))
@@ -524,7 +568,7 @@ func TestBridge_LogoutOffline(t *testing.T) {
 	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, storeKey []byte) {
 		var userID string
 
-		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, mocks *bridge.Mocks) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
 			// Login the user.
 			userID = must(bridge.LoginFull(ctx, username, password, nil, nil))
 
@@ -546,7 +590,7 @@ func TestBridge_LogoutOffline(t *testing.T) {
 		// Go back online.
 		netCtl.Enable()
 
-		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, mocks *bridge.Mocks) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
 			// The user is still disconnected.
 			require.Equal(t, []string{userID}, bridge.GetUserIDs())
 			require.Empty(t, getConnectedUserIDs(t, bridge))
@@ -556,7 +600,7 @@ func TestBridge_LogoutOffline(t *testing.T) {
 
 func TestBridge_DeleteDisconnected(t *testing.T) {
 	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, storeKey []byte) {
-		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, mocks *bridge.Mocks) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
 			// Login the user.
 			userID, err := bridge.LoginFull(ctx, username, password, nil, nil)
 			require.NoError(t, err)
@@ -584,7 +628,7 @@ func TestBridge_DeleteDisconnected(t *testing.T) {
 
 func TestBridge_DeleteOffline(t *testing.T) {
 	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, storeKey []byte) {
-		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, mocks *bridge.Mocks) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
 			// Login the user.
 			userID, err := bridge.LoginFull(ctx, username, password, nil, nil)
 			require.NoError(t, err)
@@ -608,7 +652,7 @@ func TestBridge_DeleteOffline(t *testing.T) {
 
 func TestBridge_UserInfo_Alias(t *testing.T) {
 	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, vaultKey []byte) {
-		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, vaultKey, func(bridge *bridge.Bridge, mocks *bridge.Mocks) {
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, vaultKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
 			// Create a new user.
 			userID, _, err := s.CreateUser("primary", []byte("password"))
 			require.NoError(t, err)
@@ -631,12 +675,7 @@ func TestBridge_UserInfo_Alias(t *testing.T) {
 
 func TestBridge_User_Refresh(t *testing.T) {
 	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, vaultKey []byte) {
-		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, vaultKey, func(bridge *bridge.Bridge, mocks *bridge.Mocks) {
-			mocks.Reporter.EXPECT().ReportMessageWithContext(
-				gomock.Eq("Warning: refresh occurred"),
-				mocksPkg.NewRefreshContextMatcher(proton.RefreshAll),
-			).Return(nil)
-
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, vaultKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
 			// Get a channel of sync started events.
 			syncStartCh, done := chToType[events.Event, events.SyncStarted](bridge.GetEvents(events.SyncStarted{}))
 			defer done()
@@ -662,7 +701,26 @@ func TestBridge_User_Refresh(t *testing.T) {
 	})
 }
 
+func TestBridge_User_GetAddresses(t *testing.T) {
+	withEnv(t, func(ctx context.Context, s *server.Server, netCtl *proton.NetCtl, locator bridge.Locator, storeKey []byte) {
+		// Create a user.
+		userID, _, err := s.CreateUser("user", password)
+		require.NoError(t, err)
+		addrID2, err := s.CreateAddress(userID, "user@external.com", []byte("password"))
+		require.NoError(t, err)
+		require.NoError(t, s.ChangeAddressType(userID, addrID2, proton.AddressTypeExternal))
+
+		withBridge(ctx, t, s.GetHostURL(), netCtl, locator, storeKey, func(bridge *bridge.Bridge, _ *bridge.Mocks) {
+			userLoginAndSync(ctx, t, bridge, "user", password)
+			info, err := bridge.GetUserInfo(userID)
+			require.NoError(t, err)
+			require.Equal(t, 1, len(info.Addresses))
+			require.Equal(t, info.Addresses[0], "user@proton.local")
+		})
+	})
+}
+
 // getErr returns the error that was passed to it.
-func getErr[T any](val T, err error) error {
+func getErr[T any](_ T, err error) error {
 	return err
 }

internal/certs/cert_store_darwin.go

@@ -1,4 +1,4 @@
-// Copyright (c) 2023 Proton AG
+// Copyright (c) 2025 Proton AG
 //
 // This file is part of Proton Mail Bridge.
 //
@@ -17,69 +17,411 @@
 
 package certs
 
-import (
-	"os"
+/*
+#cgo CFLAGS: -x objective-c
+#cgo LDFLAGS: -framework Foundation -framework Security
+#import <Foundation/Foundation.h>
+#import <Security/Security.h>
 
-	"golang.org/x/sys/execabs"
+// Memory management rules:
+// Foundation object (Objective-C prefixed with `NS`) get ARC (Automatic Reference Counting), and do not need to be released manually.
+// Core Foundation objects (C), prefixed with need to be released manually using CFRelease() unless:
+// - They're obtained using a CF method containing the word Get (a.k.a. the Get Rule).
+// - They're obtained using toll-free bridging from a Foundation Object (using the __bridge keyword).
+
+//****************************************************************************************************************************************************
+/// \brief Create a certificate object from DER-encoded data.
+///
+/// \return The certifcation. The caller is responsible for releasing the object using CFRelease.
+/// \return NULL if data is not a valid DER-encoded certificate.
+//****************************************************************************************************************************************************
+SecCertificateRef certFromData(char const* data, uint64_t length) {
+    NSData *der = [NSData dataWithBytes:data length:length];
+    return SecCertificateCreateWithData(NULL, (__bridge CFDataRef)der);
+}
+
+
+//****************************************************************************************************************************************************
+/// \brief Check if a certificate is in the user's keychain.
+///
+/// \param[in] cert The certificate.
+/// \return true iff the certificate is in the user's keychain.
+//****************************************************************************************************************************************************
+bool _isCertificateInKeychain(SecCertificateRef const cert) {
+    NSDictionary *attrs = @{
+        (id)kSecMatchItemList: @[(__bridge id)cert],
+        (id)kSecClass: (id)kSecClassCertificate,
+        (id)kSecReturnData: @YES
+    };
+    return errSecSuccess == SecItemCopyMatching((__bridge CFDictionaryRef)attrs, NULL);
+}
+
+//****************************************************************************************************************************************************
+/// \brief Check if a certificate is in the user's keychain.
+///
+/// \param[in] certData The certificate data in DER encoded format.
+/// \param[in] certSize The size of the certData in bytes.
+/// \return true iff the certificate is in the user's keychain.
+//****************************************************************************************************************************************************
+bool isCertificateInKeychain(char const* certData, uint64_t certSize) {
+    return _isCertificateInKeychain(certFromData(certData, certSize));
+}
+
+
+//****************************************************************************************************************************************************
+/// \brief Add a certificate to the user's keychain.
+///
+/// \param[in] cert The certificate.
+/// \return The status for the operation.
+//****************************************************************************************************************************************************
+OSStatus _addCertificateToKeychain(SecCertificateRef const cert) {
+    NSDictionary* addQuery = @{
+        (id)kSecValueRef: (__bridge id) cert,
+        (id)kSecClass: (id)kSecClassCertificate,
+    };
+    return SecItemAdd((__bridge CFDictionaryRef) addQuery, NULL);
+}
+
+//****************************************************************************************************************************************************
+/// \brief Add a certificate to the user's keychain.
+///
+/// \param[in] certData The certificate data in DER encoded format.
+/// \param[in] certSize The size of the certData in bytes.
+/// \return The status for the operation.
+//****************************************************************************************************************************************************
+OSStatus addCertificateToKeychain(char const* certData, uint64_t certSize) {
+    return _addCertificateToKeychain(certFromData(certData, certSize));
+}
+
+//****************************************************************************************************************************************************
+/// \brief Add a certificate to the user's keychain.
+///
+/// \param[in] cert The certificate.
+/// \return The status for the operation.
+//****************************************************************************************************************************************************
+OSStatus _removeCertificateFromKeychain(SecCertificateRef const cert) {
+        NSDictionary *query = @{ (id)kSecClass: (id)kSecClassCertificate,
+                                 (id)kSecMatchItemList: @[(__bridge id)cert],
+                                 (id)kSecMatchLimit: (id)kSecMatchLimitOne,
+        };
+        return SecItemDelete((__bridge CFDictionaryRef) query);
+}
+
+//****************************************************************************************************************************************************
+/// \brief Add a certificate to the user's keychain.
+///
+/// \param[in] certData The certificate data in DER encoded format.
+/// \param[in] certSize The size of the certData in bytes.
+/// \return The status for the operation.
+//****************************************************************************************************************************************************
+OSStatus removeCertificateFromKeychain(char const* certData, uint64_t certSize) {
+    return _removeCertificateFromKeychain(certFromData(certData, certSize));
+}
+
+//****************************************************************************************************************************************************
+/// \brief Check if a certificate is trusted in the user's keychain.
+///
+/// \param[in] cert The certificate.
+/// \return true iff the certificate is trusted in the user's keychain.
+//****************************************************************************************************************************************************
+bool _isCertificateTrusted(SecCertificateRef const cert) {
+    CFArrayRef trustSettings = NULL;
+    OSStatus status = SecTrustSettingsCopyTrustSettings(cert, kSecTrustSettingsDomainUser, &trustSettings);
+    if (status != errSecSuccess) {
+        return false;
+    }
+    CFIndex count = CFArrayGetCount(trustSettings);
+    bool result = false;
+    for (CFIndex index = 0; index < count; ++index) {
+        CFDictionaryRef dict = (CFDictionaryRef)CFArrayGetValueAtIndex(trustSettings, index);
+        if (!dict) {
+            continue;
+        }
+        CFNumberRef num = (CFNumberRef)CFDictionaryGetValue(dict, kSecTrustSettingsResult);
+        int value;
+        if (num && CFNumberGetValue(num, kCFNumberSInt32Type, &value) && (value == kSecTrustSettingsResultTrustRoot)) {
+            result = true;
+            break;
+        }
+    }
+    CFRelease(trustSettings);
+    return result;
+}
+
+//****************************************************************************************************************************************************
+/// \brief Check if a certificate is trusted in the user's keychain.
+///
+/// \param[in] certData The certificate data in DER encoded format.
+/// \param[in] certSize The size of the certData in bytes.
+/// \return true iff the certificate is trusted in the user's keychain.
+//****************************************************************************************************************************************************
+bool isCertificateTrusted(char const* certData, uint64_t certSize) {
+    return _isCertificateTrusted(certFromData(certData, certSize));
+}
+
+//****************************************************************************************************************************************************
+/// \brief Set the trust level for a certificate in the user's keychain. This call will trigger a security prompt.
+///
+/// \param[in] cert The certificate.
+/// \param[in] trustLevel The trust level.
+/// \return The status for the operation.
+//****************************************************************************************************************************************************
+OSStatus _setCertificateTrustLevel(SecCertificateRef const cert, int trustLevel) {
+    SecPolicyRef policy = SecPolicyCreateSSL(true, NULL); // we limit our trust to SSL
+    NSDictionary *trustSettings = @{
+        (id)kSecTrustSettingsResult: [NSNumber numberWithInt:trustLevel],
+        (id)kSecTrustSettingsPolicy: (__bridge id) policy,
+    };
+    OSStatus status = SecTrustSettingsSetTrustSettings(cert, kSecTrustSettingsDomainUser, (__bridge CFTypeRef)(trustSettings));
+    CFRelease(policy);
+    return status;
+}
+
+//****************************************************************************************************************************************************
+/// \brief Set a certificate as trusted in the user's keychain. This call will trigger a security prompt.
+///
+/// \param[in] cert The certificate.
+/// \return The status for the operation.
+//****************************************************************************************************************************************************
+OSStatus _setCertificateTrusted(SecCertificateRef cert) {
+    return _setCertificateTrustLevel(cert, kSecTrustSettingsResultTrustRoot);
+}
+
+//****************************************************************************************************************************************************
+/// \brief Set a certificate as trusted in the user's keychain. This call will trigger a security prompt.
+///
+/// \param[in] certData The certificate data in DER encoded format.
+/// \param[in] certSize The size of the certData in bytes.
+/// \return The status for the operation.
+//****************************************************************************************************************************************************
+OSStatus setCertificateTrusted(char const* certData, uint64_t certSize) {
+    return _setCertificateTrusted(certFromData(certData, certSize));
+}
+
+//****************************************************************************************************************************************************
+/// \brief Remove the trust level of a certificate in the user's keychain.
+///
+/// \param[in] cert The certificate.
+/// \return The status for the operation.
+//****************************************************************************************************************************************************
+OSStatus _removeCertificateTrust(SecCertificateRef cert) {
+    return _setCertificateTrustLevel(cert, kSecTrustSettingsResultUnspecified);
+}
+
+//****************************************************************************************************************************************************
+/// \brief Remove the trust level of a certificate in the user's keychain.
+///
+/// \param[in] certData The certificate data in DER encoded format.
+/// \param[in] certSize The size of the certData in bytes.
+/// \return The status for the operation.
+//****************************************************************************************************************************************************
+OSStatus removeCertificateTrust(char const* certData, uint64_t certSize) {
+    return _removeCertificateTrust(certFromData(certData, certSize));
+}
+*/
+import "C"
+
+import (
+	"encoding/pem"
+	"errors"
+	"fmt"
+	"unsafe"
 )
 
+// some of the error codes returned by Apple's Security framework.
+const (
+	errSecSuccess            = 0
+	errAuthorizationCanceled = -60006
+)
+
+// certPEMToDER converts a certificate in PEM format to DER format, which is the format required by Apple's Security framework.
+func certPEMToDER(certPEM []byte) ([]byte, error) {
+	block, left := pem.Decode(certPEM)
+	if block == nil {
+		return []byte{}, errors.New("invalid PEM certificate")
+	}
+
+	if len(left) > 0 {
+		return []byte{}, errors.New("trailing data found at the end of a PEM certificate")
+	}
+
+	return block.Bytes, nil
+}
+
+// wrapCGoCertCallReturningBool wrap call to a CGo function returning a bool.
+// if the certificate is invalid the call will return false.
+func wrapCGoCertCallReturningBool(certPEM []byte, fn func(*C.char, C.ulonglong) bool) bool {
+	certDER, err := certPEMToDER(certPEM)
+	if err != nil {
+		return false // error are ignored
+	}
+
+	buffer := C.CBytes(certDER)
+	defer C.free(unsafe.Pointer(buffer)) //nolint:unconvert
+
+	return fn((*C.char)(buffer), C.ulonglong(len(certDER)))
+}
+
+// wrapCGoCertCallReturningBool wrap call to a CGo function returning an error
+func wrapCGoCertCallReturningError(certPEM []byte, fn func(*C.char, C.ulonglong) error) error {
+	certDER, err := certPEMToDER(certPEM)
+	if err != nil {
+		return err
+	}
+
+	buffer := C.CBytes(certDER)
+	defer C.free(unsafe.Pointer(buffer)) //nolint:unconvert
+
+	return fn((*C.char)(buffer), C.ulonglong(len(certDER)))
+}
+
+// isCertInKeychain returns true if the given certificate is stored in the user's keychain.
+func isCertInKeychain(certPEM []byte) bool {
+	return wrapCGoCertCallReturningBool(certPEM, isCertInKeychainCGo)
+}
+
+func isCertInKeychainCGo(buffer *C.char, size C.ulonglong) bool {
+	return bool(C.isCertificateInKeychain(buffer, size))
+}
+
+// addCertToKeychain adds a certificate to the user's keychain.
+// Trying to add a certificate that is already in the keychain will result in an error.
+func addCertToKeychain(certPEM []byte) error {
+	return wrapCGoCertCallReturningError(certPEM, addCertToKeychainCGo)
+}
+
+func addCertToKeychainCGo(buffer *C.char, size C.ulonglong) error {
+	if errCode := C.addCertificateToKeychain(buffer, size); errCode != errSecSuccess {
+		return fmt.Errorf("could not add certificate to keychain (error %v)", errCode)
+	}
+
+	return nil
+}
+
+// removeCertFromKeychain removes a certificate from the user's keychain.
+// Trying to remove a certificate that is not in the keychain will result in an error.
+func removeCertFromKeychain(certPEM []byte) error {
+	return wrapCGoCertCallReturningError(certPEM, removeCertFromKeychainCGo)
+}
+
+func removeCertFromKeychainCGo(buffer *C.char, size C.ulonglong) error {
+	if errCode := C.removeCertificateFromKeychain(buffer, size); errCode != errSecSuccess {
+		return fmt.Errorf("could not remove certificate from keychain (error %v)", errCode)
+	}
+	return nil
+}
+
+// isCertTrusted check if a certificate is trusted in the user's keychain.
+func isCertTrusted(certPEM []byte) bool {
+	return wrapCGoCertCallReturningBool(certPEM, isCertTrustedCGo)
+}
+
+func isCertTrustedCGo(buffer *C.char, size C.ulonglong) bool {
+	return bool(C.isCertificateTrusted(buffer, size))
+}
+
+// setCertTrusted sets a certificate as trusted in the user's keychain.
+// This function will trigger a security prompt from the system.
+func setCertTrusted(certPEM []byte) error {
+	return wrapCGoCertCallReturningError(certPEM, setCertTrustedCGo)
+}
+
+func setCertTrustedCGo(buffer *C.char, size C.ulonglong) error {
+	errCode := C.setCertificateTrusted(buffer, size)
+	switch errCode {
+	case errSecSuccess:
+		return nil
+	case errAuthorizationCanceled:
+		return ErrUserCanceledCertificateInstall
+	default:
+		return fmt.Errorf("could not set certificate trust in keychain (error %v)", errCode)
+	}
+}
+
+// removeCertTrust remove the trust level of the certificated from the user's keychain.
+// This function will trigger a security prompt from the system.
+func removeCertTrust(certPEM []byte) error {
+	return wrapCGoCertCallReturningError(certPEM, removeCertTrustCGo)
+}
+
+func removeCertTrustCGo(buffer *C.char, size C.ulonglong) error {
+	errCode := C.removeCertificateTrust(buffer, size)
+	switch errCode {
+	case errSecSuccess:
+		return nil
+	case errAuthorizationCanceled:
+		return ErrUserCanceledCertificateInstall
+	default:
+		return fmt.Errorf("could not set certificate trust in keychain (error %v)", errCode)
+	}
+}
+
+func osSupportCertInstall() bool {
+	return true
+}
+
+// installCert installs a certificate in the keychain. The certificate is added to the keychain and it is set as trusted.
+// This function will trigger a security prompt from the system, unless the certificate is already trusted in the user keychain.
 func installCert(certPEM []byte) error {
-	name, err := writeToTempFile(certPEM)
+	certDER, err := certPEMToDER(certPEM)
 	if err != nil {
 		return err
 	}
 
-	return addTrustedCert(name)
+	p := C.CBytes(certDER)
+	defer C.free(unsafe.Pointer(p)) //nolint:unconvert
+	buffer := (*C.char)(p)
+	size := C.ulonglong(len(certDER))
+
+	if !isCertInKeychainCGo(buffer, size) {
+		if err := addCertToKeychainCGo(buffer, size); err != nil {
+			return err
+		}
+	}
+
+	if !isCertTrustedCGo(buffer, size) {
+		return setCertTrustedCGo(buffer, size)
+	}
+
+	return nil
 }
 
+// uninstallCert uninstalls a certificate in the keychain. The certificate trust is removed and the certificated is deleted from the keychain.
+// This function will trigger a security prompt from the system, unless the certificate is not trusted in the user keychain.
 func uninstallCert(certPEM []byte) error {
-	name, err := writeToTempFile(certPEM)
+	certDER, err := certPEMToDER(certPEM)
 	if err != nil {
 		return err
 	}
 
-	return removeTrustedCert(name)
+	p := C.CBytes(certDER)
+	defer C.free(unsafe.Pointer(p)) //nolint:unconvert
+	buffer := (*C.char)(p)
+	size := C.ulonglong(len(certDER))
+
+	if isCertTrustedCGo(buffer, size) {
+		if err := removeCertTrustCGo(buffer, size); err != nil {
+			return err
+		}
+	}
+
+	if isCertInKeychainCGo(buffer, size) {
+		return removeCertFromKeychainCGo(buffer, size)
+	}
+
+	return nil
 }
 
-func addTrustedCert(certPath string) error {
-	return execabs.Command( //nolint:gosec
-		"/usr/bin/security",
-		"execute-with-privileges",
-		"/usr/bin/security",
-		"add-trusted-cert",
-		"-d",
-		"-r", "trustRoot",
-		"-p", "ssl",
-		"-k", "/Library/Keychains/System.keychain",
-		certPath,
-	).Run()
-}
-
-func removeTrustedCert(certPath string) error {
-	return execabs.Command( //nolint:gosec
-		"/usr/bin/security",
-		"execute-with-privileges",
-		"/usr/bin/security",
-		"remove-trusted-cert",
-		"-d",
-		certPath,
-	).Run()
-}
-
-// writeToTempFile writes the given data to a temporary file and returns the path.
-func writeToTempFile(data []byte) (string, error) {
-	f, err := os.CreateTemp("", "tls")
+func isCertInstalled(certPEM []byte) bool {
+	certDER, err := certPEMToDER(certPEM)
 	if err != nil {
-		return "", err
+		return false
 	}
 
-	if _, err := f.Write(data); err != nil {
-		return "", err
-	}
+	p := C.CBytes(certDER)
+	defer C.free(unsafe.Pointer(p)) //nolint:unconvert
+	buffer := (*C.char)(p)
+	size := C.ulonglong(len(certDER))
 
-	if err := f.Close(); err != nil {
-		return "", err
-	}
-
-	return f.Name(), nil
+	return isCertInKeychainCGo(buffer, size) && isCertTrustedCGo(buffer, size)
 }

internal/certs/cert_store_darwin_test.go

@@ -0,0 +1,98 @@
+// Copyright (c) 2025 Proton AG
+//
+// This file is part of Proton Mail Bridge.
+//
+// Proton Mail Bridge is free software: you can redistribute it and/or modify
+// it under the terms of the GNU General Public License as published by
+// the Free Software Foundation, either version 3 of the License, or
+// (at your option) any later version.
+//
+// Proton Mail Bridge is distributed in the hope that it will be useful,
+// but WITHOUT ANY WARRANTY; without even the implied warranty of
+// MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+// GNU General Public License for more details.
+//
+// You should have received a copy of the GNU General Public License
+// along with Proton Mail Bridge. If not, see <https://www.gnu.org/licenses/>.
+
+//go:build darwin
+
+package certs
+
+import (
+	"testing"
+
+	"github.com/stretchr/testify/require"
+)
+
+func TestCertInKeychain(t *testing.T) {
+	// no trust settings change is performed, so this test will not trigger an OS security prompt.
+	certPEM := generatePEMCertificate(t)
+	require.True(t, osSupportCertInstall())
+	require.False(t, isCertInKeychain(certPEM))
+	require.NoError(t, addCertToKeychain(certPEM))
+	require.True(t, isCertInKeychain(certPEM))
+	require.Error(t, addCertToKeychain(certPEM))
+	require.True(t, isCertInKeychain(certPEM))
+	require.NoError(t, removeCertFromKeychain(certPEM))
+	require.False(t, isCertInKeychain(certPEM))
+	require.Error(t, removeCertFromKeychain(certPEM))
+	require.False(t, isCertInKeychain(certPEM))
+}
+
+// This test require human interaction (macOS security prompts), and is disabled by default.
+func _TestCertificateTrust(t *testing.T) { //nolint:unused
+	certPEM := generatePEMCertificate(t)
+	require.False(t, isCertTrusted(certPEM))
+	require.NoError(t, addCertToKeychain(certPEM))
+	require.NoError(t, setCertTrusted(certPEM))
+	require.True(t, isCertTrusted(certPEM))
+	require.NoError(t, removeCertTrust(certPEM))
+	require.False(t, isCertTrusted(certPEM))
+	require.NoError(t, removeCertFromKeychain(certPEM))
+}
+
+// This test require human interaction (macOS security prompts), and is disabled by default.
+func _TestInstallAndRemove(t *testing.T) { //nolint:unused
+	certPEM := generatePEMCertificate(t)
+
+	// fresh install
+	require.False(t, isCertInstalled(certPEM))
+	require.NoError(t, installCert(certPEM))
+	require.True(t, isCertInKeychain(certPEM))
+	require.True(t, isCertTrusted(certPEM))
+	require.True(t, isCertInstalled(certPEM))
+	require.NoError(t, uninstallCert(certPEM))
+	require.False(t, isCertInKeychain(certPEM))
+	require.False(t, isCertTrusted(certPEM))
+	require.False(t, isCertInstalled(certPEM))
+
+	// Install where certificate is already in Keychain, but not trusted.
+	require.NoError(t, addCertToKeychain(certPEM))
+	require.False(t, isCertInstalled(certPEM))
+	require.NoError(t, installCert(certPEM))
+	require.True(t, isCertInstalled(certPEM))
+
+	// Install where certificate is already installed
+	require.NoError(t, installCert(certPEM))
+
+	// Remove when certificate is not trusted.
+	require.NoError(t, removeCertTrust(certPEM))
+	require.NoError(t, uninstallCert(certPEM))
+	require.False(t, isCertInstalled(certPEM))
+
+	// Remove when certificate has already been removed.
+	require.NoError(t, uninstallCert(certPEM))
+	require.False(t, isCertTrusted(certPEM))
+	require.False(t, isCertInKeychain(certPEM))
+}
+
+func generatePEMCertificate(t *testing.T) []byte {
+	template, err := NewTLSTemplate()
+	require.NoError(t, err)
+
+	certPEM, _, err := GenerateCert(template)
+	require.NoError(t, err)
+
+	return certPEM
+}

internal/certs/cert_store_linux.go

@@ -1,4 +1,4 @@
-// Copyright (c) 2023 Proton AG
+// Copyright (c) 2025 Proton AG
 //
 // This file is part of Proton Mail Bridge.
 //
@@ -17,6 +17,10 @@
 
 package certs
 
+func osSupportCertInstall() bool {
+	return false
+}
+
 func installCert([]byte) error {
 	return nil // Linux doesn't have a root cert store.
 }
@@ -24,3 +28,7 @@ func installCert([]byte) error {
 func uninstallCert([]byte) error {
 	return nil // Linux doesn't have a root cert store.
 }
+
+func isCertInstalled([]byte) bool {
+	return false
+}

internal/certs/cert_store_windows.go

@@ -1,4 +1,4 @@
-// Copyright (c) 2023 Proton AG
+// Copyright (c) 2025 Proton AG
 //
 // This file is part of Proton Mail Bridge.
 //
@@ -17,6 +17,10 @@
 
 package certs
 
+func osSupportCertInstall() bool {
+	return false
+}
+
 func installCert([]byte) error {
 	return nil // NOTE(GODT-986): Install certs to root cert store?
 }
@@ -24,3 +28,7 @@ func installCert([]byte) error {
 func uninstallCert([]byte) error {
 	return nil // NOTE(GODT-986): Uninstall certs from root cert store?
 }
+
+func isCertInstalled([]byte) bool {
+	return false
+}

internal/certs/installer.go

@@ -1,4 +1,4 @@
-// Copyright (c) 2023 Proton AG
+// Copyright (c) 2025 Proton AG
 //
 // This file is part of Proton Mail Bridge.
 //
@@ -17,16 +17,66 @@
 
 package certs
 
-type Installer struct{}
+import (
+	"errors"
+
+	"github.com/sirupsen/logrus"
+)
+
+var (
+	ErrUserCanceledCertificateInstall = errors.New("the user cancelled the authorization dialog")
+)
+
+type Installer struct {
+	log *logrus.Entry
+}
 
 func NewInstaller() *Installer {
-	return &Installer{}
+	return &Installer{
+		log: logrus.WithField("pkg", "certs"),
+	}
+}
+
+func (installer *Installer) OSSupportCertInstall() bool {
+	return osSupportCertInstall()
 }
 
 func (installer *Installer) InstallCert(certPEM []byte) error {
-	return installCert(certPEM)
+	installer.log.Info("Installing the Bridge TLS certificate in the OS keychain")
+
+	if err := installCert(certPEM); err != nil {
+		installer.log.WithError(err).Error("The Bridge TLS certificate could not be installed in the OS keychain")
+		return err
+	}
+
+	installer.log.Info("The Bridge TLS certificate was successfully installed in the OS keychain")
+	return nil
 }
 
 func (installer *Installer) UninstallCert(certPEM []byte) error {
-	return uninstallCert(certPEM)
+	installer.log.Info("Uninstalling the Bridge TLS certificate from the OS keychain")
+
+	if err := uninstallCert(certPEM); err != nil {
+		installer.log.WithError(err).Error("The Bridge TLS certificate could not be uninstalled from the OS keychain")
+		return err
+	}
+
+	installer.log.Info("The Bridge TLS certificate was successfully uninstalled from the OS keychain")
+	return nil
+}
+
+func (installer *Installer) IsCertInstalled(certPEM []byte) bool {
+	return isCertInstalled(certPEM)
+}
+
+// LogCertInstallStatus reports the current status of the certificate installation in the log.
+// If certificate installation is not supported on the platform, this function does nothing.
+func (installer *Installer) LogCertInstallStatus(certPEM []byte) {
+	if installer.OSSupportCertInstall() {
+		if installer.IsCertInstalled(certPEM) {
+			installer.log.Info("The Bridge TLS certificate is installed in the OS keychain")
+		} else {
+			installer.log.Info("The Bridge TLS certificate is not installed in the OS keychain")
+		}
+	}
 }

internal/certs/tls.go

@@ -1,4 +1,4 @@
-// Copyright (c) 2023 Proton AG
+// Copyright (c) 2025 Proton AG
 //
 // This file is part of Proton Mail Bridge.
 //

internal/certs/tls_test.go

@@ -1,4 +1,4 @@
-// Copyright (c) 2023 Proton AG
+// Copyright (c) 2025 Proton AG
 //
 // This file is part of Proton Mail Bridge.
 //

internal/clientconfig/applemail.go

@@ -1,4 +1,4 @@
-// Copyright (c) 2023 Proton AG
+// Copyright (c) 2025 Proton AG
 //
 // This file is part of Proton Mail Bridge.
 //
@@ -21,6 +21,7 @@ import (
 	"os"
 	"path/filepath"
 	"strconv"
+	"strings"
 	"time"
 
 	"github.com/ProtonMail/proton-bridge/v3/internal/useragent"
@@ -39,10 +40,10 @@ func (c *AppleMail) Configure(
 	hostname string,
 	imapPort, smtpPort int,
 	imapSSL, smtpSSL bool,
-	username, addresses string,
+	username, displayName, addresses string,
 	password []byte,
 ) error {
-	mc := prepareMobileConfig(hostname, imapPort, smtpPort, imapSSL, smtpSSL, username, addresses, password)
+	mc := prepareMobileConfig(hostname, imapPort, smtpPort, imapSSL, smtpSSL, username, displayName, addresses, password)
 
 	confPath, err := saveConfigTemporarily(mc)
 	if err != nil {
@@ -66,26 +67,28 @@ func prepareMobileConfig(
 	hostname string,
 	imapPort, smtpPort int,
 	imapSSL, smtpSSL bool,
-	username, addresses string,
+	username, displayName, addresses string,
 	password []byte,
 ) *mobileconfig.Config {
 	return &mobileconfig.Config{
-		DisplayName:  username,
-		EmailAddress: addresses,
-		Identifier:   "protonmail " + username + strconv.FormatInt(time.Now().Unix(), 10),
+		DisplayName:        escapeXMLString(username),
+		EmailAddress:       escapeXMLString(addresses),
+		AccountName:        escapeXMLString(displayName),
+		AccountDescription: escapeXMLString(username),
+		Identifier:         escapeXMLString("protonmail " + username + strconv.FormatInt(time.Now().Unix(), 10)),
 		IMAP: &mobileconfig.IMAP{
-			Hostname: hostname,
+			Hostname: escapeXMLString(hostname),
 			Port:     imapPort,
 			TLS:      imapSSL,
-			Username: username,
-			Password: string(password),
+			Username: escapeXMLString(username),
+			Password: escapeXMLString(string(password)),
 		},
 		SMTP: &mobileconfig.SMTP{
-			Hostname: hostname,
+			Hostname: escapeXMLString(hostname),
 			Port:     smtpPort,
 			TLS:      smtpSSL,
-			Username: username,
-			Password: string(password),
+			Username: escapeXMLString(username),
+			Password: escapeXMLString(string(password)),
 		},
 	}
 }
@@ -98,6 +101,8 @@ func saveConfigTemporarily(mc *mobileconfig.Config) (fname string, err error) {
 
 	// Make sure the temporary file is deleted.
 	go func() {
+		defer recover() //nolint:errcheck
+
 		<-time.After(10 * time.Minute)
 		_ = os.RemoveAll(dir)
 	}()
@@ -117,3 +122,13 @@ func saveConfigTemporarily(mc *mobileconfig.Config) (fname string, err error) {
 
 	return
 }
+
+// escapeXMLString replace all occurrences of the 5 characters `&`, `<`, `>`, `"` and `'` by their respective escaped version as per the XML spec.
+// https://www.w3.org/TR/xml/#syntax
+func escapeXMLString(input string) string {
+	result := strings.ReplaceAll(input, `&`, `&amp;`)
+	result = strings.ReplaceAll(result, `<`, `&lt;`)
+	result = strings.ReplaceAll(result, `>`, `&gt;`)
+	result = strings.ReplaceAll(result, `"`, `&quot;`)
+	return strings.ReplaceAll(result, `'`, `&apos;`)
+}

internal/clientconfig/applemail_test.go

@@ -0,0 +1,38 @@
+// Copyright (c) 2025 Proton AG
+//
+// This file is part of Proton Mail Bridge.
+//
+// Proton Mail Bridge is free software: you can redistribute it and/or modify
+// it under the terms of the GNU General Public License as published by
+// the Free Software Foundation, either version 3 of the License, or
+// (at your option) any later version.
+//
+// Proton Mail Bridge is distributed in the hope that it will be useful,
+// but WITHOUT ANY WARRANTY; without even the implied warranty of
+// MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+// GNU General Public License for more details.
+//
+// You should have received a copy of the GNU General Public License
+// along with Proton Mail Bridge. If not, see <https://www.gnu.org/licenses/>.
+
+//go:build darwin
+
+package clientconfig
+
+import (
+	"testing"
+
+	"github.com/stretchr/testify/require"
+)
+
+func TestEscapeXMLString(t *testing.T) {
+	require.Equal(t, escapeXMLString(`abc&&''""<<>>def`), `abc&amp;&amp;&apos;&apos;&quot;&quot;&lt;&lt;&gt;&gt;def`)
+}
+
+// This test requires human interaction (user configuration profile installation prompt). It is for debugging purpose and is disabled by default.
+func _TestInstallCert(t *testing.T) { //nolint:unused
+	require.NoError(
+		t,
+		(&AppleMail{}).Configure(`127.0.0.1`, 1143, 1025, true, false, `user&>>`, `<<abc&&'"def>>`, `user&a`, []byte(`ir8R9vhdNXyB7isWzhyEkQ`)),
+	)
+}

internal/constants/constants.go

@@ -1,4 +1,4 @@
-// Copyright (c) 2023 Proton AG
+// Copyright (c) 2025 Proton AG
 //
 // This file is part of Proton Mail Bridge.Bridge.
 //
@@ -33,9 +33,12 @@ var (
 	// Version of the build.
 	Version = "0.0.0"
 
-	// Revision is current hash of the build.
+	// Revision is build time commit hash.
 	Revision = ""
 
+	// Tag is build time git describe.
+	Tag = ""
+
 	// BuildTime stamp of the build.
 	BuildTime = ""
 
@@ -44,6 +47,9 @@ var (
 
 	// DSNSentry client keys to be able to report crashes to Sentry.
 	DSNSentry = ""
+
+	// BuildEnv tags used at build time.
+	BuildEnv = ""
 )
 
 const (

internal/constants/host_default.go

@@ -1,4 +1,4 @@
-// Copyright (c) 2023 Proton AG
+// Copyright (c) 2025 Proton AG
 //
 // This file is part of Proton Mail Bridge.
 //

internal/constants/host_qa.go

@@ -1,4 +1,4 @@
-// Copyright (c) 2023 Proton AG
+// Copyright (c) 2025 Proton AG
 //
 // This file is part of Proton Mail Bridge.
 //

internal/constants/update_default.go

@@ -1,4 +1,4 @@
-// Copyright (c) 2023 Proton AG
+// Copyright (c) 2025 Proton AG
 //
 // This file is part of Proton Mail Bridge.
 //