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

From one user I have received a debug log of the current beta where it apparently crashes in the dtor of the mail object after send.

Cool! Thanks for testing :-)

Thanks for the help,

I still don't have any clue what could be wrong here.

I can't reproduce this. I sent myself a Mail with capitalized "Andre.Heinecke@intevation.de" while my key only has an identity for "andre.heinecke@intevation.de" and it worked as expected:

Mh, that is strange and indeed a bug if that is so. GpgOL should do some simple normalisation which should prevent exactly such a problem. I'll look into it.

With 3.1 ( https://www.gpg4win.org/version3.1.html ) the problem should be gone. We still have to block outlook when the inline editor is used but that left no artifacts in the past. And if a Mail Window is opened we do not block outlook anymore. We only disable it to show a modal dialog.

As this is easy to test and I tested it myself I think I can mark it as resolved.

Thanks for your help / report.

With Gpg4win 3.1.0 ( https://files.gpg4win.org/Beta/gpg4win-3.1.0-beta-current.exe ) GpgOL no longer uses Kleopatra for signing. So this problem can no longer exist.

I'm lowering the priority to Normal. I've done a lot of GpgOL work and Testing for the upcoming 3.1.0 release and have not seen this problem.

We have this now. There might be bugs but in general this works.

I installed 3.1.0-beta and tested all use cases, everything is working properly now.

Should work with the current beta: https://files.gpg4win.org/Beta/gpg4win-3.1.0-beta-current.exe Although the window mangement is still a bit "iffy" but we at least switch back the focus.

I've uploaded a beta for the upcoming 3.1.0 Version: https://files.gpg4win.org/Beta/gpg4win-3.1.0-beta-current.exe

Version 3.1.0 now supports sign & encrypt and sign only for G Suite accounts as long as there are no attachments on the mail.

Great.
I'll wait for v3.1.0 then.

From the log I can see that GpgOL picks up the wrong "Sender" address. It thinks that you sent the mail yourself and then the mail address <> signature does not match. So it is not flagged as Trusted.

I've started adding a workaround, but shelved it for now. Any workaround would not work for plain signed mails and would not be interoperable with other clients.

Ok, thanks!

Sadly this is a known problem, the workaround is to unselect the mail and then move / modify it through the right click menu.