GPG OL is crashing when sending message from a outlook profile created by gsuite tool
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Description

As a Google GSuite client, when using outlook I had to install the GSuite Sync. Every time I try to send an e-mail the Outlook 2016 at Windows 8, the mail client crashs and at the restart it report as a GPGOL problem and disable it.

To test, i create two profiles, one by using the Sync and other by using the manual configuration. Every e-mail sent by the one with Sync crashs the outlook (deterministic), and every e-mail sent by the one without the sync works correctly. I beleave that there is some inconsistence into GSuite Sync with GPGOL.

brunoslalmeida renamed this task from GPG OL is crashing when sending message from a outlook profile created by gsuit tool to GPG OL is crashing when sending message from a outlook profile created by gsuite tool.

If someone could help me on how to debug on outlook, I could produce more information about this bug.

werner triaged this task as Normal priority.Oct 10 2017, 6:30 PM
werner added a subscriber: werner.

That seems to be a conflict between the two extensions. We need to look deeper into that so learn why it could go wrong and whether there is a way to work around the conflicts.

I’m facing this issue too..

I'm also facing the same issue here.

DanielSL rescinded a token.Oct 10 2017, 9:11 PM
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i'm facing the same problem. Would love to see this problem solved

jccruz added a subscriber: jccruz.

Oh, God, someone please solve this problem. It is so annoying. Tried everything I could, installed and uninstalled the softwares and accomplished nothing.

Levi added a subscriber: Levi.Oct 10 2017, 9:20 PM

I'm also facing the same issue here.

aheinecke claimed this task.
aheinecke raised the priority of this task from Normal to High.
aheinecke added subscribers: stashimi_frank, aheinecke.

Already handled the crash in: T3540

I need to get a test setup with google sync. Any chance someone has a test account for me?

I'll try to register myself for the free trial period.

So I went through the google app sync setup and now have a test account.

I could reproduce the missing sender from T3540 and fixed that with above revision.
I could not reproduce the problems with recipients from T3540. I added them to the address book etc. and it just worked.

Picture or it did not happen:

Please replace your gpgol.dll in <gpg4win_install_dir>\bin (or for 64 bit outlook \bin_64) with the latest one (according to your outlook architecture) from https://files.gpg4win.org/Beta/gpgol/ It's currently 2.0.4-beta15
and test again / let me know what works and what does not work.

Thanks for your help and patience and apologies for the problems!

Noticed one problem already. Google rewrites the PGP/MIME Mails we send into a multipart/mixed mail with the PGP Data as an attachment. I'll see if I can find a workaround :-/

You're the hero!!!!

I just verified that it detects the sender as well as the recipient now and lets me select the certs via kleo correctly.
Also noticed the issue you mentioned. The ascii armored signature arrived as attachment on the receoiver's side.

Good job.

Already handled the crash in: T3540

I need to get a test setup with google sync. Any chance someone has a test account for me?

I'll try to register myself for the free trial period.

Sorry for taking so long to answer you back. If you have any problem with Google GSuit, I can create an account for you.

Noticed one problem already. Google rewrites the PGP/MIME Mails we send into a multipart/mixed mail with the PGP Data as an attachment. I'll see if I can find a workaround :-/

I had this problem with Google when it used its new API (Gmail API with OAuth). I solved this by using the smtp and not the Gmail API to send e-mail. For some unknown reason, the API change the PGP/MIME of the message. I will test and see if it is the same problem.

Noticed one problem already. Google rewrites the PGP/MIME Mails we send into a multipart/mixed mail with the PGP Data as an attachment. I'll see if I can find a workaround :-/

This problem occurs also when receiving an e-mail from Google Sync (that use Gmail API).

I tried a bit to find a Workaround. As far as I can tell Outlooks built in S/MIME Support does not even work with GSync. If anyone can send S/MIME encrypted or validly signed mails trough GSync please let me know.

I'll work on PGP/Inline (no-mime) support next. Then we can use this for GSync accounts.
I hate it because that will bring back all the brokenness in attachment / encoding handling etc. that PGP/MIME solves and it will not be a good user experience. :-/

aheinecke closed this task as Resolved.Nov 29 2017, 3:35 PM

As the crash is fixed and awaits release I think this issue is resolved. But that does not mean that we support G Suite sync. I don't see a quick fix :-/

For the Problems in general and a discussion what we could do there I opened T3545 . I'm currently undecided what to do with that. For the next release It would probably be best to either switch back to the old interface for GSync accounts or just bail out / don't offer encryption / signing.
For a discussion about that please use T3545

For T3662 (PGP/Inline problem with Microsoft Exchange Online) I had to change the code used to send PGP/Inline.

As my GSync Trial account ran out It would be great if someone here could try out 2.0.6-Beta9 from http://files.gpg4win.org/Beta/gpgol/ to confirm that sending PGP/Inline from GSuite Sync accounts still works.