I just tried the newest beta and I can confirm that sending Office attachments does work for me with this version.

Added gpgol and gpg4win project tags as this is important for these projects.

I was unable to figure out what the difference is between the handling of Office files and other files and why it comes to this error.

I can reproduce the issue and give it high priority. This is a curious problem of Outlook triggered by the improved send code in Gpg4win 3.1.3.

Here's the debug log file.

Thanks for your answer. So i think we must wait for the Update and downgrade to 3.1.2.

Da wir eine internationale Software sind bevorzugen wir in diesem Tracker Englisch. Ich hoffe das ist ok.

Thanks for the report. I was not aware of this but Indeed the fix should be easy. I think I already know the cause ;-)

Address book integration is in. What is still needed is to respect the overrides in the interactive key selection dialog.

I'm looking at my personal Inbox on both computers.
I received the encrypted mails, before I connected computer B with my Account
And yes, I'm using an exchange connection.

Thanks for the details. I tried to reproduce it but again for me it works. Still I give this high priority as this can be a blocker in deploying GpgOL and we should fix it for the next release.

I have additionally the problem, that signed and encrypted S/MIMI messages are handled by GPGOL even if S/MIME support is disabled.

The original reporter in the gpg4win-forums reports that this does not work reliably. :-/

Gpg4win-3.1.3 was released.

Gpg4win-3.1.3 was released. This issue can be closed. Hurray!

Gpg4win-3.1.3 was released.

Gpg4win-3.1.3 was released.

Gpg4win-3.1.3 was released.

Gpg4win-3.1.3 was released.

Gpg4win-3.1.3 was released.

Gpg4win-3.1.3 was released

Gpg4win-3.1.3 was released.

Gpg4win-3.1.3 was released.

https://www.gpg4win.org/version3.1.3.html < beta28 has the fix. If nothing untoward happens this will be the final version to be released tomorrow.

I have to revert the changes. The problem is that with attachments included Outlook must parse the S/MIME Mail. The code I've added to handle the PGP/Inline in GpgOL would result in hidden attachments as Outlook no longer properly parses the S/MIME Mail, we only decrypt the body and so attachments are gone.

I can't reproduce it. I don't get the Properties have changed dialog.

It's not super good but now when S/MIME is disabled we also look into the body of S/MIME mails to check for the PGP Inline message marker.

I've tried again with different Versions to rerproduce this issue and I can't reproduce it.

I did not find any differences regarding junk mail. So I believe that this is fixed with T3459

This is done now. Didn't help with crashes but is a good thing anyway IMO.

This is done now.
I had a slight hope that this might help with random crashes as the COM is now under less load but it did not help.

This was fixed by adding a new reference mechanism with cebe6484acaa250858affa3d854ef2b25cecd59f (Where I acidentally mangled the commit message.

Hooray!

We are actually in the final release preparation and just waiting for GnuPG 2.2.10. If everything goes well it will be released this week. If not, next week.

Sweet, thank you! Any estimate on when that might come out?

yes

excellent - will this be includedin gpg4win 3.1.3?

Thanks. I can work with that. It is indeed clearly visible what the "Sent on behalf of" address is. So it makes sense to check that, too.

Sent two messages to the test mailinglist. Please let me know if you need / want more.

Yes that would work for me and the pgp key is the right one. Thanks!

Actually, I can add you to a test mailinglist and send you a signed message tomorrow, would that work?

Ok! If outlook shows it we should verify it.

Hi Andre!

With -beta24 the crash on send should also be gone. I've removed the option for the workaround as I expect that it is no longer necessary. (Yeah I'm an Optimist :-P )

T4026 is a bit related. I'm suprised that the signature check for mailman mails works at all for you ;-)

Thanks for the input. GpgOL should check against what outlook shows as the "From" Address. In your case: What does Outlook show? Is it "info@example.org" or "puppets-bounces" ?

No response so closing as invalid.

I'm not sure if it's exactly the same case, but:

Hi, gpg4o does not send PGP/MIME (the proper format for including attachments and no encoding problems). As such it does not have the Problem described here. You can use "Send PGP Mails without attachments as PGP/Inline" in the options of GpgOL to have something similar. This will also work for Kopano.

how is the actual state of this point? Is it solved?

With certified keys the automation is working as expected.

Got a new OL 2013 test setup where this was finally reproducible for me.

The option you mean is "Disable non-blocking encrypt / sign", correct?
It's english in the german dialogue, btw.

The crash on send should be avoidable by checking "Disable async encryption" in the options.
Yesterday I got a new OL 2013 test system with which I can reproduce the crash. So that will be fixed or worked around for the next release.

no. Outlook 2013 reproducably crashes on sending and won't toggle
encryption on.

Sure, this should work, local keys are preferred.

But can't I simply use the keys in my local keyring?

No you can not use an "external" Web Key Directory. The point is that the provider (your domain) should be the source of the keys as it already manages the mail account. ( For more info see: https://wiki.gnupg.org/WKD )