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...

For reference here is @mcgrof's dump in a directly readable format:

00:29:33.472844 IP 192.168.4.7.10218 > 192.168.4.1.domain: 53039+ SRV? _pgpkey-https._tcp.hkps.pool.sks-keyservers.net. (65)
00:29:33.879268 IP 192.168.4.1.domain > 192.168.4.7.10218: 53039 FormErr 0/0/0 (65)
00:29:33.880719 IP 192.168.4.7.10218 > 192.168.4.1.domain: 51133+ Type0 (Class 8448)? _pgpkey-https._tcp.hkps.pool.sks-keyservers.net. (66)
00:29:33.902115 IP 192.168.4.1.domain > 192.168.4.7.10218: 51133 FormErr 0/0/0 (65)

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 T3378#106503, @raysatiro wrote:

I assume it goes in %APPDATA%\gnupg\gpg-agent.conf.

In T3378#106440, @werner wrote:

Can someone please add

disable-check-own-socket

to gpg-agent.conf to test whether this is the cause for the problem. ( note that I asked for this also in T3401)

Sorry for the delay, been a busy busy couple of weeks..

the warning message is probably too cryptic.

Many thanks! This bug is fixed in Gpg4win 3.0.1.

Can you please install the new version and check if the error still persists?

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.

IIRC, I red some hints on using a powershell module to switch the output to binary. I tries to find that mode, or weel its source or scrip) but to no success. It seems to be a common problem with powershell because it is not a real shell as we are used to (where many commands have a /b switch but that switching could also be done using setmode() ).

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.

I can reproduce the problem.

@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!

Setting this to resolved until we get reports to the contrary.

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.

Can someone please add

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 introduce GnuPG to my friend, yesterday. I saw this problem. It's on Windows 7, gpg4win 3.0.1 and enigmail.
Looking through this report, Windows 7 is common factor.

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:

Dirmngr should no longer run as a system service. It's now started with user privileges on demand. The

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

To keep the tracker clean I'm closing this as a duplicate of T3476 since both problems are very much related. GpgEx would print Internal Error if Kleopatra crashes or behaves unexpectedly.

Here you are

The only way I can think of that this fails if that there are some old files from a gpg4win installation that was not cleanly removed lying around and failing to start.

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.

tried to answer in the text with ###:

Normal priority as this should be looked into but is not dramatic.

What Kind of File were you attempting to Verify (e.g. S/MIME or openpgp, detached or embedded). Ideally if it was a public file I could try to reproduce.

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.

So the error handling is improved now. We restore the original body on error and show the error in the tooltip of the GpgOL Status Icon.

I can reproduce it if I send and receive with Outlook 2010. I have some working mails in my Outlook 2010 though, this is the reason why I first thought that it did not happen for me. Looking at the same mails in Outlook 2016 works fine.

Thanks for the detailed report. I can't reproduce this behavior. Neither on my Outlook 2010 test system or my Outlook 2016 test system.
I can see several verification errors in the Log. First todo: Communicate the error and restore the original body.

So the selftest fails and then Kleopatra crashes? Mmh I'll try to break my gpg4win installation in a similar manner.

Priority Low as it's partly a question and We can't reproduce (for me keygen is reasonably fast)

@PaulJ this sounds like a different problem. For you it does not show. In this report the pinentry open's in the background for file sign / encrypt.

I'm giving this normal priority because I can't reproduce this.

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,

After having a look at the code base I guess this behaviour is intentional.

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.

Well the key resolution handling and dialog needs some love. Thats on the todo. But this issue here can be resolved as the op says.

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 :-)

The symbols are coming from the message class and are only updated when the mail is viewed and afterwards unselected. It might be that Outlook sometimes does not update the symbol when the message class changes after the message has been read once.