diff --git a/go.mod b/go.mod
index 90e20e5d..54265d9a 100644
--- a/go.mod
+++ b/go.mod
@@ -7,7 +7,7 @@ require (
 	github.com/Masterminds/semver/v3 v3.2.0
 	github.com/ProtonMail/gluon v0.16.1-0.20230525065316-a08bb823bbca
 	github.com/ProtonMail/go-autostart v0.0.0-20210130080809-00ed301c8e9a
-	github.com/ProtonMail/go-proton-api v0.4.1-0.20230602072524-9e72c2541c15
+	github.com/ProtonMail/go-proton-api v0.4.1-0.20230605082423-67859aec0317
 	github.com/ProtonMail/gopenpgp/v2 v2.7.1-proton
 	github.com/PuerkitoBio/goquery v1.8.1
 	github.com/abiosoft/ishell v2.0.0+incompatible
diff --git a/go.sum b/go.sum
index 39183bec..bc13cb34 100644
--- a/go.sum
+++ b/go.sum
@@ -40,8 +40,8 @@ github.com/ProtonMail/go-message v0.13.1-0.20230526094639-b62c999c85b7 h1:+j+Kd/
 github.com/ProtonMail/go-message v0.13.1-0.20230526094639-b62c999c85b7/go.mod h1:NBAn21zgCJ/52WLDyed18YvYFm5tEoeDauubFqLokM4=
 github.com/ProtonMail/go-mime v0.0.0-20230322103455-7d82a3887f2f h1:tCbYj7/299ekTTXpdwKYF8eBlsYsDVoggDAuAjoK66k=
 github.com/ProtonMail/go-mime v0.0.0-20230322103455-7d82a3887f2f/go.mod h1:gcr0kNtGBqin9zDW9GOHcVntrwnjrK+qdJ06mWYBybw=
-github.com/ProtonMail/go-proton-api v0.4.1-0.20230602072524-9e72c2541c15 h1:gZYur1RURw2LxrOXU6rYM+SdX3G2m9i93w/1uyfPa3k=
-github.com/ProtonMail/go-proton-api v0.4.1-0.20230602072524-9e72c2541c15/go.mod h1:+aTJoYu8bqzGECXL2DOdiZTZ64bGn3w0NC8VcFpJrFM=
+github.com/ProtonMail/go-proton-api v0.4.1-0.20230605082423-67859aec0317 h1:Mo293UO7CfX1mL+jrBoSrftvhEyq6hyRDia2d6+Kx9U=
+github.com/ProtonMail/go-proton-api v0.4.1-0.20230605082423-67859aec0317/go.mod h1:+aTJoYu8bqzGECXL2DOdiZTZ64bGn3w0NC8VcFpJrFM=
 github.com/ProtonMail/go-srp v0.0.7 h1:Sos3Qk+th4tQR64vsxGIxYpN3rdnG9Wf9K4ZloC1JrI=
 github.com/ProtonMail/go-srp v0.0.7/go.mod h1:giCp+7qRnMIcCvI6V6U3S1lDDXDQYx2ewJ6F/9wdlJk=
 github.com/ProtonMail/gopenpgp/v2 v2.7.1-proton h1:YS6M20yvjCJPR1r4ADW5TPn6rahs4iAyZaACei86bEc=
diff --git a/internal/user/imap.go b/internal/user/imap.go
index b6257cba..2b7c3bd0 100644
--- a/internal/user/imap.go
+++ b/internal/user/imap.go
@@ -37,6 +37,7 @@ import (
 	"github.com/ProtonMail/proton-bridge/v3/pkg/message/parser"
 	"github.com/bradenaw/juniper/stream"
 	"github.com/bradenaw/juniper/xslices"
+	"github.com/sirupsen/logrus"
 	"golang.org/x/exp/slices"
 )
 
@@ -357,6 +358,12 @@ func (conn *imapConnector) CreateMessage(
 		err = fmt.Errorf("%v: %w", err, connector.ErrMessageSizeExceedsLimits)
 	}
 
+	if apiErr := new(proton.APIError); errors.As(err, &apiErr) {
+		logrus.WithError(apiErr).WithField("Details", apiErr.DetailsToString()).Error("Failed to import message")
+	} else {
+		logrus.WithError(err).Error("Failed to import message")
+	}
+
 	return msg, literal, err
 }
 
diff --git a/internal/user/user.go b/internal/user/user.go
index ec010ba3..3d7077ba 100644
--- a/internal/user/user.go
+++ b/internal/user/user.go
@@ -463,7 +463,15 @@ func (user *User) SendMail(authID string, from string, to []string, r io.Reader)
 		return ErrInvalidRecipient
 	}
 
-	return user.sendMail(authID, from, to, r)
+	if err := user.sendMail(authID, from, to, r); err != nil {
+		if apiErr := new(proton.APIError); errors.As(err, &apiErr) {
+			logrus.WithError(apiErr).WithField("Details", apiErr.DetailsToString()).Error("failed to send message")
+		}
+
+		return err
+	}
+
+	return nil
 }
 
 // CheckAuth returns whether the given email and password can be used to authenticate over IMAP or SMTP with this user.