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GpgOL: Async encryption can keep the message window open in a defunct state
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Description

With the Async encryption code I saw it multiple times that the message window stayed open when sending a message and then you could click send a second time.

This is confusing at the very least. Because I also saw once that this leaked plaintext when hitting send a second time I will disable Async encryption again for the Gpg4win-3.1.16 release.

Event Timeline

aheinecke created this task.

maybe related is that the problems only occured when I had enabled draft encryption.

In T6701 it was reported that this also occurs if we block outlook long enough in the send event and not only if we disable the window like we do with the async encryption.

ebo edited projects, added gpgol; removed Restricted Project.Dec 12 2025, 3:10 PM
ebo moved this task from Backlog to Triage on the gpgol board.

I'm quite sure, that I have seen this multiple times on current versions. Not sure, if one could send it again, I think at least the body is empty.

alexk lowered the priority of this task from High to Normal.
alexk added a subscriber: alexk.

We need tests to reproduce this.

I have no idea how to reproduce this, there is no pattern. It could as well be, that some server side thing is involved, which is not under our control.
Either I'm lucky and it just happens while the logs are enabled, or I'll try some auto loop with appium one day.

Luckily I tested T5374: GpgOL: Can't move a signed mail in Outlook from In-Mail folder to any other folder afterwards and found out, that with my current settings in gpg4win-5.0.2-beta2 @ win11 I can reproduce this every time by sending signed only mails (pgp and smime does not matter).
Regarding my settings, I only activated the security dialog:

To reproduce:

  1. I created a new mail
  2. set From to edward, To to Ted
  3. waited for autosecure to set encrypt/sign state
  4. removed encryption (so it's signed only)
  5. added a subject and a mail content
  6. sent the mail
  7. confirmed the security dialog => the mail compose window remained

In the remaining window, the mail content is removed:

I can't resend the mail though.

gpgol.log (call trace + data)