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Maniphest T6865

Email will be sent encrypted after draft was saved in encrypted state although encryption is disabled
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Description

A user reported a problem that appears when the user wants to redirect an encrypted message. The user could read the email but when he redirected it to another person the second person got this error message:
"Kein geheimer Schlüssel gefunden der zu der Nachricht passt. Sie ist mit den folgenden Schlüsseln lesbar: <the key of the user>"

The user redirects emails inline and uses MS 365.

He also found out that the error occurs when he enabled the option “Entwürfe von abgesicherten Mails mit diesem Schlüssel verschlüsseln” and followed these steps:

  1. Write a new email or select that he wants to redirect an email
  2. Enable encryption
  3. Wait until the draft is saved automatically or save it manually
  4. Disable encryption
  5. Send the email

Details

Version
4.1.0

Event Timeline

cklassen created this task.Dec 5 2023, 9:34 AM
• werner added projects: Too Old, Support.Dec 18 2023, 6:04 PM
• werner added a subscriber: • werner.

Assuming 4.1.0 means gpg4win - this version is too old. The user should update and re-open the bug with more details if it persists.

• werner closed this task as Resolved.Dec 18 2023, 6:05 PM
• werner claimed this task.
jh reopened this task as Open.Dec 27 2023, 9:10 AM
jh added a subscriber: jh.

Hi,

i am not the original owner of this bug, but facing the same issue.

My current version of Gpg4win is 4.2.0.

The issue occurs when the checkbox to encrypt draft emails is turned on. This is one of the essential details.

So, to reproduce the issue, first write a new email and enable (at least, signing is optional) the encryption.

Now wait until the draft will be saved automatically or save it manually via Ctrl+S. The email will show up as encrypted in the draft emails.

Now continue editing the email by removing the encryption. This step is essential, too.

When the email is sent, there will be no prompt for the encryption passphrase. I would assume, that the email was sent unencrypted. In the inbox of the recipient (i wrote the email to myself in ths case, but it can be reproduced with other recipients, too), the email shows up as encrypted and a password prompt pops up.


Additionally, the sent email shows up as encrypted, too.

(Surprisingly, the email can be accessed via the Outlook web version, even though it seems to be encrypted, but this is just a side note.)

Finally, here are some files, that might be helpful for reproduction:
Sent email:

Gesendet.eml13 KBDownload

Received email:
Empfangen.eml16 KBDownload

GpgOL log file:
gpgol.txt60 KBDownload

I use the legacy Outlook desktop app on Windows 10.

Thank you in advance for your support. If there are any details missing, just let me know.

• werner removed • werner as the assignee of this task.Jan 2 2024, 9:42 AM
• werner edited projects, added gpgol; removed Too Old.
aheinecke triaged this task as Normal priority.Jan 15 2024, 10:41 AM
aheinecke edited projects, added Restricted Project; removed Support.
aheinecke added a subscriber: aheinecke.

Thank you for the detailed report. I will look into it.