It is unlikely that we will fix it. The OL behaviour is just too flaky. It might be possible to do this in the no-preview mode in a more robust way.

I could not reproduce this issue with Gpg4win 4.4.1 and did not see it with Gpg4win-5.0.0-beta345, either.

I could not reproduce this issue with Gpg4win 4.4.1 (which should have it).

tested with Gpg4win 5.0Beta-336

This one made me curious because updating the should be UI solved, and it is incredibly dangerous to mess with that. It is super easy to get random crashes when you invalidate the UI too much. It took me ages to get that "stable enough". But also technically an appointment request is a mail. And thanks to dan (afair), KMail can sign and encrypt invitations. And at least for signed invitations they are displayed as appointment so I looked into this a bit out of curiousity.

In T4836#132493, @aheinecke wrote:

Thank you for the detailed report.

We recently had a similar problem with S/MIME Mails. T4543 I think that we can apply the same fix we did for S/MIME also for OpenPGP. So I give this high priority as I think that this can be easily fixed and is a big problem in mixed environments.

was fixed in gpgol 2.5.15

Test with KF6 (open, close, open config dialog).

see T7098

Outlook problem that can't be fixed.
Workaround possible (First start message, then add recipients).

Fixed in most cases.
Edge cases will be examined further.

I suspect there's also a bug somewhere between qt and windows involved here: The overlay is supposed to be modal to the composer window, so it shouldn't be possible to move the overlay behind the compositor. This is probably the reason why the overlay is forced to stay on top in the first place...

Well it kind of works but it is a bit ugly and the encoding in the "Encrypt" message is broken:

An easy solution seems to be to just tell the overlay to not be always on top. It still blocks the outlook window, but other windows can then be shown on top of it.

Fixed:

turned out that not the flowcrypt encryption is the issue here. The cause seems to be the usage of Proofpoint "Email Warning Tags".

Gpg4win is a community version and we may or may not apply Authenticode signatures. You can do that yourself, after having checked our OpenPGP release signature. You may however be interested in GnuPG Desktop, which comes with full support and also Authenticode signature.

Forgot a screenshot:

Yes. I did only one test though, with an inline PGP mail sent with Claws.

Yes it does. I even tested it yesterday.

Looks like plain old inline PGP. Does GpgOL even support inline PGP?

https://flowcrypt.com/
They use OpenPGP.js according to https://flowcrypt.com/docs/getting-started/overview/openpgp-compatibility.html
They have a cooperation with Google.

What is FlowCrypt?

turns out that this seems to be a timing issue/race condition and disappears if more debug output is added

with VSD-Beta-3.3.90.10:

With VS-Desktop-3.3.90.6-Beta:

this is not yet in master and not included in the current testbulid

My above comment is true for the main case described in the ticket, cancelling decryption followed by "permanently decrypt".

I see no improvement in VSD-Beta-3.3.90.6, the issue persists.
Btw: Is this maybe related to T7596: GpgOL: Draft is not decrypted after cancelling decryption once?

After further testing:
The new level 3 icon is shown for most test cases. This ticket here is only for the new icon, therefore I'm setting this to done. I'll make a new ticket for the cases where the level is not detected correctly.

with Version VS-Desktop-3.3.90.6-Beta: