Funny behaviour with GpgOL, Exchange Online and occasional PGP/MIME breakage

Yes, it’s the old “This is a broken PGP/MIME message from MS-Exchange…” problem again.

This time it happens only when using GpgOL to first read the message.

As in, disable the GpgOL add-in in Outlook → messages don’t break even if you first open them in Outlook and then later in Thunderbird (IMAP) or some such.

Obivous downside that you can’t decrypt/verify in Outlook then.

Messages first opened with GpgOL get the blue padlock icon and keep it even after GpgOL is unloaded and Outlook restarted.

Messages first opened with Thunderbird - or web access - can be reread, decrypted and verified with GpgOL without breakage, but don’t get the padlock icon ever.

Yes, Outlook with GpgOL can be open and doesn’t break the message unless the “first read” is done with it.
(Also seems to include race conditions where “already read” status hasn’t gotten to Outlook in time, which is further evidence that this happens in Outlook and not on the server.)

Gpg4win 3.1.3, Office 365 ProPlus latest monthly with the new look.

Thanks, we probably have not tested this with Exchange Online as we mostly test with Cached Exchange.

I’ll look into it but this might be hard to fix as it sounds like the problem is in the interaction between Exchange and Outlook.

No change in behaviour on this one with latest updates - Gpg4win 3.14, Outlook “1809 (Build 10827.20181 Click-to-Run)”.

… and again, now with Gpg4win 3.1.5 and Outlook “1810 (Build 11001.20108 Click-to-Run)” - no change, still breaks.


Yes. I did not yet get around to look into it (although I’m not optimistic I could solve it easily anyway),… still on my TODO. Sorry :frowning:

Eh, as long as it’s a known issue and not forgotten… Click-to-Run is a moving target anyway.