diff --git a/internal/smtp/user.go b/internal/smtp/user.go
index 39655e17..62d31407 100644
--- a/internal/smtp/user.go
+++ b/internal/smtp/user.go
@@ -20,9 +20,11 @@
 package smtp
 
 import (
+	"bytes"
 	"encoding/base64"
 	"fmt"
 	"io"
+	"io/ioutil"
 	"mime"
 	"net/mail"
 	"strings"
@@ -319,6 +321,12 @@ func (su *smtpUser) Send(returnPath string, to []string, messageReader io.Reader
 		return nil
 	}
 
+	if ok, err := su.isTotalSizeOkay(message, attReaders); err != nil {
+		return err
+	} else if !ok {
+		return errors.New("message is too large")
+	}
+
 	su.backend.sendRecorder.addMessage(sendRecorderMessageHash)
 	message, atts, err := su.storeUser.CreateDraft(kr, message, attReaders, attachedPublicKey, attachedPublicKeyName, parentID)
 	if err != nil {
@@ -329,12 +337,6 @@ func (su *smtpUser) Send(returnPath string, to []string, messageReader io.Reader
 	su.backend.sendRecorder.setMessageID(sendRecorderMessageHash, message.ID)
 	log.WithField("messageID", message.ID).Debug("Draft was created successfully")
 
-	if ok, err := su.isTotalSizeOkay(message, atts); err != nil {
-		return err
-	} else if !ok {
-		return errors.New("message is too large")
-	}
-
 	// We always have to create a new draft even if there already is one,
 	// because clients don't necessarily save the draft before sending, which
 	// can lead to sending the wrong message. Also clients do not necessarily
@@ -534,7 +536,7 @@ func (su *smtpUser) Logout() error {
 	return nil
 }
 
-func (su *smtpUser) isTotalSizeOkay(message *pmapi.Message, attachments []*pmapi.Attachment) (bool, error) {
+func (su *smtpUser) isTotalSizeOkay(message *pmapi.Message, attReaders []io.Reader) (bool, error) {
 	maxUpload, err := su.storeUser.GetMaxUpload()
 	if err != nil {
 		return false, err
@@ -542,8 +544,14 @@ func (su *smtpUser) isTotalSizeOkay(message *pmapi.Message, attachments []*pmapi
 
 	var attSize int64
 
-	for _, att := range attachments {
-		attSize += att.Size
+	for i := range attReaders {
+		b, err := ioutil.ReadAll(attReaders[i])
+		if err != nil {
+			return false, err
+		}
+
+		attSize += int64(len(b))
+		attReaders[i] = bytes.NewBuffer(b)
 	}
 
 	return message.Size+attSize <= maxUpload, nil
diff --git a/test/accounts/fake.json b/test/accounts/fake.json
index 60bea18a..79ba3742 100644
--- a/test/accounts/fake.json
+++ b/test/accounts/fake.json
@@ -2,23 +2,28 @@
     "users": {
         "user": {
             "ID": "1",
-            "Name": "user"
+            "Name": "user",
+            "MaxUpload": 26214400
         },
         "user2fa": {
             "ID": "2",
-            "Name": "user2fa"
+            "Name": "user2fa",
+            "MaxUpload": 26214400
         },
         "userAddressWithCapitalLetter": {
             "ID": "3",
-            "Name": "userAddressWithCapitalLetter"
+            "Name": "userAddressWithCapitalLetter",
+            "MaxUpload": 26214400
         },
         "userMoreAddresses": {
             "ID": "4",
-            "Name": "userMoreAddresses"
+            "Name": "userMoreAddresses",
+            "MaxUpload": 26214400
         },
         "userDisabledPrimaryAddress": {
             "ID": "5",
-            "Name": "userDisabledPrimaryAddress"
+            "Name": "userDisabledPrimaryAddress",
+            "MaxUpload": 26214400
         }
     },
     "addresses": {
diff --git a/unreleased.md b/unreleased.md
index 2f8de02f..efdd11bd 100644
--- a/unreleased.md
+++ b/unreleased.md
@@ -5,6 +5,17 @@ Changelog [format](http://keepachangelog.com/en/1.0.0/)
 ## Unreleased
 
 ### Added
+* GODT-958 Release notes per eaach update channel.
+* GODT-906 Handle RFC2047-encoded content transfer encoding values.
+* GODT-875 Added GUI dialog on force update.
+* GODT-820 Added GUI notification on impossibility of update installation (both silent and manual).
+* GODT-870 Added GUI notification on error during silent update.
+* GODT-805 Added GUI notification on update available.
+* GODT-804 Added GUI notification on silent update installed (promt to restart).
+* GODT-275 Added option to disable autoupdates in settings (default autoupdate is enabled).
+* GODT-874 Added manual triggers to Updater module.
+* GODT-851 Added support of UID EXPUNGE.
+* GODT-928 Reject messages which are too large.
 
 ### Removed
 
@@ -17,6 +28,3 @@ Changelog [format](http://keepachangelog.com/en/1.0.0/)
 * GODT-900 Remove \Deleted flag after re-importing the message (do not delete messages by moving to local folder and back).
 * GODT-908 Do not unpause event loop if other mailbox is still fetching.
 * Check deprecated status code first to better determine API error.
-* GODT-732 Fix usage of fontawesome
-* GODT-915 Bump go-imap dependency and remove go-imap-specialuse dependency.
-* GODT-928 Reject messages which are too large.