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GpgOL: Setting category or flagging crypto mails is not possible
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Setting a category on a crypto mail or Flagging it does not work.

This is because GpgOL blocks changes to crypto mails to avoid that decrypted content is sent back to the server and to avoid the temporary changes GpgOL makes (e.g. parsing PGP/MIME) from being saved, which would result in a broken mail structure.

An idea which might work:

  • Detect such a change in the PropertyChange event
  • Close the mail with discard changes.
  • Open the mail again (complicated)
  • Don't parse it this time.
  • Replay the change that was made (complicated).
  • Close the mail with save.
  • Open the mail again.
  • This time decrypt it.

In the past I've tried similar things but I could not get it to work properly.



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I have a workflow now that does this without the openings. The mail is kept open by Outlook anyway when the properties are changed.

Here is what I tried:

It worked really nice for one mail I had in exchange, but for others it did not work properly. Somehow the flag change was corrupted. Probably because the prop changes were called after the close. So we might really have to do the buffer / replay step.

I recently noticed that the old workaround by setting a kategory when it is not visible in the messagelist does not work on a default Outlook 2204 anymore. This raises the priority of this issue.

aheinecke raised the priority of this task from Normal to High.Nov 3 2022, 3:11 PM
aheinecke lowered the priority of this task from High to Normal.May 15 2023, 12:04 PM

With the recent commit the old workaround works reliably again.

A user also report this problem with Microsoft365 and Outlook Versions 2302 and 2208. (Exchange is the latest online-Version.
Assuming current Gpg4win v4.2.0)

The effect ist that mails cannot be selected for followup reminders.

Yes they can, the workaround, which GpgOL even suggests in the error message is that the mail may not be visible as plain text while changing flags or categories. This usually means that you have to select a different mail and then use right click on the mail you wish to mark for followup or add a category to. The whole problem is that while the plaintext is visible in Outlook we have to prevent changes to the mail from beeing synced to the server or otherwise it will also sync the plaintext.

aheinecke raised the priority of this task from Normal to High.Jan 15 2024, 3:53 PM

With the recent commit the old workaround works reliably again.

This is no longer true. Maybe another change later on changed it but currently the right click workaround does not work anymore. The only thing that works is setting flags by using the icon when the mail is not opened. I am not sure what broke it. Maybe I can run a bisect.

A workaround which (currently) works for flagging and categories both is:

  • Mark a not selected mail by clicking on the flag. Do not use the context menu via the right mouse button! It will thereby be assigned the default flag ("Today").
  • Switch to "Tasks".
  • Change the flag date of a not selected mail / task via its context menu. You can also add a category this way.