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.

Hi Andre

I'm not a fan of memoryhole. To say my criticism in one sentence: "Memoryhole is trying to sell the hide of the boar before it has been hunted."

The only other add-in that I use is Skype, but I`ve disabled that and re-uploaded the log. We are using Exchange 2010 SP3

Thanks. Error is there:

Thanks, file attached

That is weird, I've never heard of that before.

The button shows and I can select Sign or Encrypt but they don't register / stay selected they just have a grey highlighted background whilst hovering over them... they do not toggle / stay selected.

What do you mean by "Does nothing"? The button should toggle and then when you send the mail kleopatra should show a dialog to select the signing / encryption keys.

Hi aheinecke,
I did some tests with 2.0.7-beta10 and still found some issues.
The message I attached as a test case in previous comment is now properly handled, I see no "signature.asc" attachment and message is correctly tagged as trusted sender; this test message was sent from Evolution and I sent it to myself (sorry for not pointing this out before).

My test works now with this commit.

I think the problem is with the selction change event. When we query for selection item (1) we trigger an itemLoad event which apparently causes this behavior. I've disabled everything else in our event handling code so we don't touch the mail at all (non crypto mails we never touch much).

Thanks for the test and the example mail. Should also be fixed now.
While testing I also noticed that the sender email address was also not parsed correctly for these kind of mails and added some code to fix that.

I just tested version 2.0.7-beta8 x64 and I can confirm the bug is fixed, GpgOL can decrypt messages properly. Messages also appear to be properly signed.

Thank you. With that message I could reproduce the problem and have a fix. I now get to decryption failed / no secret key as it should be.

You can find the message attached.
Message has been saved from Outlook 2013.

Thanks for your report and analysis.

My first GUI Idea does not work. From the Ribbon I don't see a way to find the currently used account. I could only look at all accounts that are configured and check the WKS publishing state for all of them.

This is coming along nicely. It might take longer then with Kleopatra if the key is large (as the new resolver does a full keylisting on every start) but that should be OK and we have plans to optimize that anyway.

In my tests this is resolved with the commits mentioned here.

I think the reason for this is not Exchange Online but that I was using two explorer Windows and switched between Mails while the decryption on the slow exchange folder was still running. This triggered an invalidate_ui while the parsing was active and that then triggered a write / unload just like in T3523

My current idea is that if GpgOL detects that the provider supports a web key service and one of the following is true:

So I tried this on Outlook 2016 MSO (16.0.4639.1000) 32-Bit

Steps 1. and 2. are now implemented in the async-enc branch of GpgOL. The keyresolver patches are updated for me and partially commited.