We had similar report back in 2015, but it was not fixed in GnuPG (possibly, card reader problem):
https://lists.gnupg.org/pipermail/gnupg-users/2015-September/thread.html#54345

Indeed. Since Gpg4win-3.0 Gpg4win uses the "official" GnuPG-w32 installer. This installer is bundled with Gpg4win and extracted during installation into the temporary directory and executed from there. So your problem is likely that GnuPG is not installed. As GnuPG is the core component of Gpg4win this will lead to a broken setup (although the error should be detected so I'll leave this issue open for that problem.

Hi,
this is intended behavior. KLEOPATRA_LOGDIR is a development / testing setting and it can be useful to look into which data is sent to GnuPG.
Please disable Kleopatra logging as described in:
https://www.gpg4win.org/doc/en/gpg4win-compendium_29.html

Alright, I need to weight in with something that may possibly be influencing the failure of the December-01-2017 build to operate correctly over here; since this issue is related to sockets, and I have set up a rather unusual security apparatus on my system ("unusual" as far as computers regularly running GPG are concerned, and that only to my personal experience, meaning no reliable statistics or anything), I think it's worth mentioning that my firewall (Sygate Personal Firewall Pro) is configured to be very restrictive and that virtually anything that utilizes tcp or udp is being routed through socks5 via ProxyCap, and that neither application is currently allowing GPG to have access to any address but localhost (there's a reason for this and has got nothing to do with GPG itself, but that's part of a different discussion).

@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.

There is request to add support for ssh-certs to gpg-agent: T1756. Right now gpg-agent can only extract the public key from the certificiates and nothing more. The gpg-agent speaks the ssh-agent protocol and as such does not know anything about files uses by ssh to store certificates.

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

:-(

Ok here's an update.

Superb! Testing gnupg-2.2.3_171201.exe as I type, and it's already working past the time it would normally cease to respond :)

The registry key does not exist on my system, and neither does the c:\program files (x86)\GnuPG\bin directory. There is only the Share directory under c:\program files (x86)\GnuPG\

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.

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.

The error is fixed with "disable-check-own-socket"
If someone is interested for next times, the log-file "gpg-agent.log" is on the path "C:\Users\<my user>\AppData\Local\VirtualStore\Program Files (x86)\Mozilla Thunderbird\".

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

Adding Windows again because on Unix it is unlikley that our close will block. A documented blocking behavior is only defined for STREAMS

Yeah, that looks correct. Good catch. The bug exhibits itself when gpg-agent checks its own socket. In this case gpg-agent is both, client and server, and due to our userland multi-threading we get blocked. The suspend/resume things makes the deadlock more likely. Note that we have the same problem on Unix.

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.

Thanks everyone. I think that the problem is identified and fixed in libassuan.

Update: It was my mistake (typical beginners failure): I had to create gpg-agent.conf instead of usig gpg.conf.
Adding disable-check-own-socket resulted in the right behavior, till now:
After some time-out, GpgOL asks for password again and decrypts the content as expected.

I am using an Antergos Linux (Arch Linux).

Please do not paste such long debug messages - they are not helpful. Please try to explain the error. From what I can see from that long dump the DNS server failed.

Indeed, this was lost by switching to the new dialog. Fixed with: https://commits.kde.org/kleopatra/005a28149fcb7f318676de47aee3014fc83b3f78

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

Fixed with https://cgit.kde.org/kleopatra.git/commit/?id=59ebe7da257131757f98e77912e39b3fd14ae3af Kleopatra was too agressive in the dialogs and always tried to stay on top. This makes sense for the Certificate selection dialog in GpgOL but not for the file dialog.

Suppose a client which connects stopped task of server on Windows. In this situation, if the client blocks on closesocket, that is, some user space work is needed for server side for closing socket of client side, this bug can be explained.

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

If disable-check-own-socket can stop hanging, D454: assuan_close with nPth could be related.

I have created the file "gpg-agent.conf" in the path "C:\Users\<my user>\AppData\Roaming\gnupg\" with the following content:

It's working for me now with that config file as well so far. I'll keep watching too.

I added "disable-check-own-socket" to gpg-agent.conf .
Since 8 hours no "hanging".
I will watch it furthermore...

Could confirm a similar behavior with Windows 7 and Outlook 2010 using GPG4Win 3.0.1.
Time frame for loosing the decryption ability is about one hour or more.
Setting disable-check-own-socket in gpg.conf (didn't find gpg-agent.conf) resulted in "no data" error on all
encrypted e-mails.

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 :-/

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...

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.