T2854 is a duplicate of this but contains more up to date information. So I'm closing this issue.

Does this still happen with gpg4win-3.0.2?

Gpg4win 3.0.2 is released which contains even more fixes for GpgOL -> Resolving this. Please let us know if you still have Problems that are not tracked here.

The option now has the following logic:

• If encrypted is selected and the message is not signed.

and

• If the message has no attachments.

and

• If the option for inline sending is enabled

The problem was with a special attachment that had no file extension. Fixed now.

I can't reproduce this with the above steps. It is sadly a known issue that moving crypto mails does not work as long as they are viewed. (T3459) But for me opening any unencrypted mail and moving it. Or first opening an encrypted mail and then moving an unencrypted mail works.

This ticket can be closed. No further issue with email decryption after applying the provided patch

I looked into it. The problem is that attachments are opened as "Read Only" so we can't change the message class or handle it ourself. Once opened there is no apparent way to change the message to read only. Only if the message containing the attachment is marked as modifyable:

I tried to reproduce this with current GpgOL and it just worked. Even if I connected Enigmail to Exchange (Outlook.com).

@patoberli This looks very much like a crash I also observed on close and fixed with 1d0660fa53d357247ac84545f9259244a1d9400c the crash has nothing to do with the hang but thanks for the feedback anyway.

I finally had a crash again today, when I tried to close outlook.
I was running the debug log for several days now, until it finally crashed. Using gpg4win 3.0.1.
Here from the debug file:
*removed entries for privacy reasons*
12:28:46/19196/oomhelp.cpp:remove_category: category 'GpgOL: Verschlüsselte Nachricht' not found.
12:28:46/19196/mail.cpp:parsing_done:882: tracepoint
12:28:46/19196/mail.cpp:parsing_done:885: tracepoint
12:28:46/19196/gpgoladdin.cpp:gpgoladdin_invalidate_ui: Invalidating ribbon: 1D363A70
12:28:46/19196/mail.cpp:parsing_done:900: tracepoint
12:28:46/18768/parsecontroller.cpp:~ParseController
12:28:46/18768/mimedataprovider.cpp:~MimeDataProvider
12:28:46/18768/attachment.cpp:~Attachment
12:28:46/18768/mimedataprovider.cpp:~MimeDataProvider
***here I closed Outlook, but Outlook froze. I then killed the process in Windows.
12:34:02/19196/windowmessages.cpp:gpgol_hook: WM_CLOSE windowmessage for explorer. Closing all mails.
12:34:02/19196/mail.cpp:close_all_mails:1084: tracepoint
12:34:02/19196/returned from invoke

I've tested the fix and so far I found no problems with decryption and email rendering.
If you want I can report back here, after using GgpOL several more days testing the fix in day-to-day usage, and then if everything is fine we can close this ticket.
Thank you very much for your time.

We now read the headers as a stream. This fixes the detection of the content type for your example mail. It now correctly fails for me with "No Secret Key".

Received a test message and I understand it now. The header lines in the test mail are so large that they cannot be queried as a single property (out of memory because the max is pretty low, 4k or so) but have to be accessed through a stream interface. Many of the headers relate to Thread and In Reply To etc. so this explains why the problem only happens on reply.
I think I can quickly fix it.

A new installer with an updated libassuan is now available. To download gnupg-2.2.3_171201.exe please go to https://gnupg.org/download/ . If you had the disable-check-own-socket in your gpg-agent.conf, please remove it so that we can really see whether that version fixes the problem.

Many improvements since dec 2016 to gpgol. Latest master is much more stable (needs a Gpg4win release)

Yes please you can send it directly to mailto://aheinecke@intevation.de
If you want to encrypt it my key is 94A5C9A03C2FE5CA3B095D8E1FDF723CF462B6B1

I am very happy to hear that! Thanks.

After a week with the current version, including a registry cleanup, I had no crashes in Outlook. At the moment it seems to be running stable.

To sum up: Outlook can't decrypt a reply, although it can decrypt a direct email from the same sender.
Another thing I just noticed: once Outlook receives the reply (the one it can't decrypt), I can no longer move emails to other folders. If I deactivate GpgOL plugin, I can move the messages again.
Can I pm you the saved message ?

Better to fail loudly instead of silently breaking.

For now I've added messages to make it clear to the user that most actions won't work with G Sync.
Better to fail loudly instead of silently breaking.

I can no longer reproduce this. We had another report about this were we also tested this and it's ok with recent GpgOL 2.x versions. -> Resolved

Does not happen for current GpgOL versions and OL < 2010 support in GpgOL is no longer maintained -> resolved

It would be very helpful if you could export ("Save As") such a mail in Outlook and attach it here / send it to me. I don't have to be able to decrypt it but I would probably be able to figure out why it's not detected as a crypto mail.

The connection is a POP3 connection. Email server is a 3rd party email service provider. I doubt is an Exchange server (I believe they run a Linux server).
Switching to a different mail and back makes no difference - no email body displayed for the encrypted email.

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 :-/

Priority High as we should decide for the next release in which direction we should move.

Fantastic! I have these following issues:

Thanks for the confirmation.

Hi, sorry for coming back so late due to lack of time - but good news is: With GPGol 2.0.4-beta15 decryption now also works for us, great! Now we only have to check for a Outlook 2016 stability issue...

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.

In T3424#106481, @aheinecke wrote:

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 :-/

In T3424#106481, @aheinecke wrote:

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 :-/

In T3424#106451, @aheinecke wrote:

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.

You're the hero!!!!

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 :-/

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

@aheinecke From a first glimpse, I think we got it. Great work!
I replaced both versions of gpgol.dll as adviced (surprisingly /bin was locked, I expected /bin_64 ).
Thereafter Outlook decrypted all "old" message instantly and without any problems.
Thanks for the effort you spent and the fast reaction time!

Already handled the crash in: T3540

Thanks for the efforts. I will subscribe there to be up to date :-)

Oops I just noticed that this was already reported in T3424 which I somehow overlooked. Let's handle it there as there are more subscribers in that report and it's older.

So both your mails did show the exact same behavior for me. The PGP MESSAGE was shown in the mail and not attempted to decrypt.

Two versions of the same message as shown in the comment of 24th Nov.

I did some experiments with HTML Mails, Leading Text, Trailing Text etc. Everything worked fine for me.

In T3537#106396, @Xv wrote:

I have some progress and a step back.
Turns out that one of the installed plugins was causing the problem: "PDF Converter 7.1 Outlook Add-in".
I disabled all plugins (except GpgOL) and then enabled them back one by one.
With PDF Converter add-in disabled I'm now able to see the decrypted email body (sent from myself).

Can someone please add

Hi, thanks for the test. This sounds a bit like T3378 if the central component "gpg-agent" hangs everything relying on it may also hang. :-/

We have similar reports in our message board.

I put it at high priority because i want to check / fix this before the next release.

Ok I'm pretty sure that the Google MAPI provider is the problem because it likely has some different Data structures.
For Sender we already have three fallbacks as it's saved differently for Exchange over MAPI, Exchange Active Sync and IMAP. So we probably need another fallback for Google Sync >.<

Thank you, too for the report and testing.

Tested GpgOL 2.0.4-beta6 with Outlook 2010 32bit and Outlook 2013 32bit on Win 10 1709 64bit.

I have some progress and a step back.
Turns out that one of the installed plugins was causing the problem: "PDF Converter 7.1 Outlook Add-in".
I disabled all plugins (except GpgOL) and then enabled them back one by one.
With PDF Converter add-in disabled I'm now able to see the decrypted email body (sent from myself).

I use the Google Sync plugin to connect with our company Google Apps account. It also synchronizes the calendar entries as well as all other special stuff.
I'm quite sure that the standard POP/IMAP mechanisms in Outlook might not deliver the sender's address (however the receipient's address is contained in the logs above - my googlemail.com address).

I'm using the same Outlook 16.0.0.8625 on Windows 10 with a Gmail Account over IMAP and I have the Google Apps Sync plugin enabled. Everything works fine :-(
What is your senders account? Is that also GMail or something different. In the log I only see that the recipient is GMail.

I'm currently triaging. I give this high priority even if it is testing. We probably need a new GpgOL release soon as there were already some bugs fixed (e.g. Selecting many messages)

Thanks.
So GpgOL can neither figure out the sender's address nor the recpients. It then fails to do crypto because kleo does not know who it should encrypt to.

For now low priority until we receive additional information. From the report now I don't really understand the problem. Maybe T3459 ? as the report mentiones moving mails.

Done. Now Outlook does not crash anymore, but GPGOL emits an error dialog:

12:33:30/13972/oomhelp.cpp:get_oom_int: Property 'BodyFormat' not found: 0x80040108
12:33:30/13972/oomhelp.cpp:get_oom_string: Property 'HTMLBody' not found: 0x80040108

Here you are

Strange, do you have any other addons? Maybe some interference.

Indeed the PGP Inline handling should be more robust. If there is leading of following text it should not error out. But as there will always be problems with that I really recommend that you use a standard format (PGP/MIME) to communicate. Then the key would be just an attachment that could be imported in Kleopatra and all the data would be encrypted / signed.

Normal priority for now until we get more reports of this. For now we have to assume that while this problem is disastrous it happens rarely as we did not get many reports about this.

Thank you very much for your good and detailed report.

I'm closing this as a duplicate of T3459 even if this bug is older we used it to discuss side topics.

Hi, sorry this is a known issue. To quote the README:

I have installed the update now @JochenSaalfeld and will observe the behaviour over the coming days.
Somehow my Outlook in combination with the plugin messed with the registry. I could only permanently re-enable the plugin after removing all related registry entries in HKEY_CURRENT_USER. Otherwise it would not load on start anymore even if activated by me.

Thanks for the test!

Hello Jochen,

It could depend on the formatting in Outlook (changing hyphens etc.), e.g.
-----BEGIN PGP MESSAGE----- looks sometimes different in Messages.

Great, I'll do it :)

I fixed the problem with multiselection that caused a very similar log for me. The fix is now in 2.0.4-beta6

I'm pretty sure I've fixed it. It would be great if you could try with the latest beta (currently 2.0.4-beta6) from https://files.gpg4win.org/Beta/gpgol/ (just replace your gpgol.dll in the gpg4win/bin or bin_64 folder with the one from there. To confirm that it's fixed.

As I reported this myself and fixed it. -> resolved.

I think this can be resolved.
GpgOL in gpg4win 3.0 supports HTML Mails. There is no extra setting which variant is preferred for multipart/alternative mails because GpgOL reads that setting from Outlook and prefers the same that Outlook would prefer.

I can reproduce a similar behavior when selecting all mails in a large folder. This was for T3433 It's not a loop it's just a huge load of "Read" events Outlook sends GpgOL and GpgOL looks at every mail.

Thanks. I'll give that a go. The only issue here is that it takes quite a long, random time to happen so chances are a successful fix is one where I never revisit this ticket :-)

Indeed indeed. I can reproduce and see that GpgOL is very active when many mails are selected. This is a regression, it worked with an older MIME enabled version. I'll look at it.