I got an Idea how to improve the situation here. But its very complex and might break Outlook even for unencrypted mails. So it's very invasive.

Ok I tested with Exquilla. I configured an Exchange account once through Thunderbirds built-in account (IMAP) and once with Exquilla

Thanks for the report.
I clarified the title a bit to include exchange / exquila.

Let's use the new issue as the problem is described completely there and it makes it more clear.

I already created a new issue for this in the new version of gpg4win (v3.1.0) with GpgOL v2.1.0. This is the issue: T3917.

You can close the report.
I'm working with a restricted user and I installed gpg4win-3.1.0 with admin rights, probably didn't work so well.

( Apart from the part that was moved out to T3895 )

3.1.0 is released and this issue is to our knowledge fixed.

3.1.0 is released and this issue is to our knowledge fixed.

3.1.0 is released and this issue is to our knowledge fixed.

3.1.0 is released and this issue is to our knowledge fixed.

3.1.0 is released and this issue is to our knowledge fixed.

3.1.0 is released and this issue is to our knowledge fixed.

3.1.0 is released and this issue is to our knowledge fixed.

I think you are running in the infamous T3459 "As long as the decrypted content of a crypto mail is loaded a mail can't be moved" You have to unselect the mail and then move it without opening it. E.g. by right clicking it. I know this is horrible and it's a major problem but I don't see how we can fix it in our architecture. As we replace the mail content with the decrypted stuff we have to prevent "Write" Events by Outlook. For Move if you block a write event, the move fails. But we don't have any idea in our addon when a write comes from a move. I spent a lot of time on this and have not yet found a good solution. But I think the workaround is kinda ok.

The Bug is here that the Error is not shown properly. In the log:

With the changes in 3.1.0 I think this is acceptable enough that we can move further improvements to this to a lower priority.
We only support PGP/Inline (no-mime), warn if an attachment is also added. A user could send attachments encrypted on a file basis.

I've opened T3895 for a permanent decryption / permanent removal of attachments. Maybe something for 3.2.0 ;-)

When an attachment of a crypto mail is removed it now leads to a warning.

In my tests it does work nicely now. We detect the "Send Again" state and correctly handle it. Sign / Encrypt is preselected depending on the state of the original mail. Even works with attachments.

Never seen the crash again.

Accidentally mixed up the ticket number. The correct commits for this ticket are:

Oops. I confused the ticket numbers rO34f6bb73882e: Implement send again for crypto mails. Would be the correct commit for this ticket.

Right, outlook.com is often problematic, although it might be a generic Exchange 2016 problem. Outlook.com and Exchange 2016 behave much the same.

I'm not sure about that (Bug in Evolution), because I see ist only in E-Mails send by Evolution via Mircosoft (outlook.com) and not if Mails werden send by Evolution via Google (gmail.com).

I've got an example mail. The problem is that the mail itself is "Content-Type: multipart/mixed; boundary="_003_DB4PR08MB01092D175DE8C1861B5D0BC197BF0DB4PR08MB0109eurp_"
"

I'll go for a warning / error for now and see if I can fix the renumbering.

In fact, renumbering of attachments happens also by just viewing them repeatedly. This likely causes multiple copies somewhere, reducing disk space.

Thanks for the report and the spelling fixes :-)

Thanks for the report.

This problem should be gone with Gpg4win-3.1.0-beta48. While I could not reproduce it I've tried to fix it and changed the hard error to a debug log in case something is unexpected here. I believe that this is safe.

I tried to reproduce this again, using S/MIME Mails, installing gpg4win 2.x etc. It did not crash for me :-/

I doubt that I will be able to fix this. The problem is that for Outlook we build the signed mail structure, which is a multipart MIME message. If you receive such a mail with a non crypto client you see the plain text and a pgp-signature attachment. That is why Outlook shows it as "attachment".

Normal prio as I don't think that this is a regression.

Thanks for trying out the beta. I was about to open an issue about this as someone in the forum reported the same thing. https://wald.intevation.org/forum/message.php?msg_id=5759

Mr. Heinecke, to make sure, please note that despite the thread title these crashes happened with 3.1.0. beta 38. It would be sad if you do all of the tests and checks with 3.0.3

Apologies for not replying to your mail directly. I've marked it in my INBOX to do the test with 3.0.3 first but have not gotten around to it.

Funny thing, it worked for some time, now it's reproducably crashing again. This might be the better log file.

So, this is tested with 3.1.0 beta 38, reproducable crash

I answered by mail in this fashion:

Fixed with: https://commits.kde.org/libkleo/5b93bddf468b6c067fe062131aee726ed4aa6928

rO4c5eed308829 fixes this.

Basic support is in. Maybe we should open a task on how to improve it.

It's two bugs working hand in hand here.

Playing around with this a bit: I can get messages to pass if I set the content type of our MOSS attachment to multipart/encrypted .
The problematic thing there is that there is a comment in the code that explicitly states that multipart/signed is needed to activate MSOXSMIME. So we have to be careful, maybe even check the Server Version somehow as I don't want to break older stuff.

Thanks for your report. Sadly I cannot reproduce this, I went back in my archives and even mails from 2015 / touched by Gpg4win 2.x work without a problem.

Thanks. After seeing this report I ran a spellchecker on the translation and found some more typos ;-) Will be fixed in the next version.

I'm closing this as I've got confirmation that one crash was fixed by disabling async encryption again. And a class of general "Crash when encrypting" bugs that were related to the communication between Kleopatra and GpgOL no longer exists as Kleopatra is no longer used when encrypting from GpgOL in gpg4win 3.1.0.

Thanks for testing and the confirmation / praise ;-)

Hi Andre,
AWESOME! Thanks a lot. It works and it’s also faster. GREAT!!!
Jacques

From: aheinecke (Andre Heinecke) [mailto:noreply@dev.gnupg.org]
Sent: March 21, 2018 2:41 AM
To: Jacques Latour <Jacques.Latour@cira.ca>
Subject: [Task] [Changed Status] T3847: Pinentry-qt pop up not appearing when I send a signed/encrypted email

aheinecke changed the task status from "Open" to "Testing".
aheinecke triaged this task as "Normal" priority.
aheinecke added projects: gpgol, gpg4win.
aheinecke added a comment.

Hi,

I'm not 100% certain but I think that it is likely that your problem is fixed with the upcoming 3.1 version. We have reworked how GpgOL encrypts there a bit ( T3509https://dev.gnupg.org/T3509 )

Could you please try out the beta of the upcoming version https://www.gpg4win.org/version3.1.html and confirm that the problem is either still there or gone?

Thanks!

TASK DETAIL
https://dev.gnupg.org/T3847

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To: aheinecke

Cc: aheinecke, latour_jacques, Mak, gp_ast

This is an automated email from the GnuPG development hub. If you have registered in the past at https://bugs.gnupg.org/ your account was migrated automatically. You can visit https://dev.gnupg.org/ to set a new password and update your email preferences.

I'm not 100% certain but I think that it is likely that your problem is fixed with the upcoming 3.1 version. We have reworked how GpgOL encrypts there a bit ( T3509 )

I got beta feedback which after analysis showed that parts of the encrypt changes in 3.1 that would have addressed this lead to crashes. So we had to disable it for now and block Outlook again as temporary blocking is better then "random" crashing :-((

Nope. The corner widget is the suggested way in outlook and users are used to it / accept it.

Works now with and without attachment and with encryption / without encryption (formerly without encryption it would add the original crypo message as attachments).

This is fixed by no longer using kleopatra for this ( T3509 )

So I implemented a way to forward mails with attachments. TODO here:

Attached Patch:

Hi @aheinecke
I Can confirm, its working for me fine now.
thanks
Martin