Hi Arthur,
sorry for the late reply:

Outlook 2010 has new code for supporting OpenPGP and S/MIME,
we will tackling the problem differently there.
I think that the last code for GPgOL for Outlook 2007 uses
encryption.

If this is still relevant for you: Can you retest?

Hi,

as the extended support period of Outlook 2003 ended in 2014,
we will not get around fixing this for Outlook 2003.

Please open a new issue, if you encounter problems with a more recent version.

Best,
Bernhard

Since the last activity on this report, GpgOL was changed a lot.
Probably the original reporter does not use the Windows/Outlook combination
anymore. Thus closing this report.

Reading about
http://www.heise.de/security/meldung/Erpressungs-Trojaner-verschluesselt-mit-PGP-3116677.html

made me think that signing all binaries may not be the best idea. For our
installer we can rule out that it does something malicious as we control what it
does. So signing it is fine. Same goes probably for GpgOL etc.

But the actual encryption stuff (libgcrypt / gnupg) can, of course, be used for
malicious purposes. So there would be the potential for malware using binaries
signed by us. This could hurt our reputation. (technically in terms of Windows
Code Signing Reputation or Anti Virus software)

At least something we should keep in mind while thinking about changes to what
we sign.

MDK7MX, did you retry ?

File? No hardware token?

I would rather add a "Sign all binaries" installed by us capability to the
packaging process then a special case handling for GpgOL. Especially for the
Uninstaller this would make sense at it requires privileged execution and is
currently unsigned.

But this would mean that we either need to split up the packaging process to
first create the binaries and on a different system (with the code signing
certificate available) create the NSIS Packages.

Or that we expose the CodeSigning certificate to the build system, which
probably makes the most sense as the build system already should be a secured
environment and we only build / execute code which we verified.

I could imagine implementing this as a configure option --with-codesigning-cert
or something thats optional during the build and which you can provide with the
certificate file.

since Outlook 2007 there is no Word editor option anymore. We will not add
support for this to Outlook 2003 as Outlook 2003 is End of Life.

Sorry that this bug was never fixed.

Regards,
Andre

Great to hear that! And again let me Thank YOU for your incredible patience and
assistance with logs to help track down / fix this problem. This was really a
nasty bug.

After installing gpg4win 2.3.0 (GpgOL 1.3.0) I had no more crashes.
Thanks for your fix.

Sorry that there has been no response on this but we did not have time to work
on gpgOL.

GpgOL for Outlook 2003 is no longer maintained and support for this in gpg4win
is likely to be dropped soonish.

I'm closing this as nobug to help us clean up the bugtracker. The word editor is
not supported in Outlook 2003 and we will not add support for this. Sorry.

Uhm five years and not reply ;-) Sorry but we did not have much time to work on
GpgOL and the little time we had we spent on Outlook 2010 and later (which is a
different codebase)

The code for 2003 and 2007 is still basically unmaintained. We are looking into
the possibility to remove 2003 support and use the 2010 and later codebase for
2007, too. From your debug output it looks like you are using exchange. This is
not supported for the < 2010 addon. (It is supporeted in the current development
version that will be part of gpg4win 3.0.0)

So you can either switch to Outlook 2010 or later (and for now use the gpg4win
3.0.0 test version) ( https://wiki.gnupg.org/Gpg4win/Testversions ) or hope that
we will enable that codebase for 2007, too.

Sorry that I am marking this as nobug but we will not fix this for 2007 only and
in later versions it already works.

This is fixed in GpgOL master.

Fixed with rev. b879f5b

I wonder if this is a Problem for the new version that can send through
exchange. Available from ( https://wiki.gnupg.org/Gpg4win/Testversions ) We look
up the sender address with exchange a bit differently and I think it should
match the actual SMTP address used now.

The updated translation is part of gpg4win 2.3.0

I think this was fixed in 2.2.3 or so. (The dll search) so this should work now.
I'm currently testing mostly on Windows 10 and there are no problems with
regards to that of which I am aware. So I'm resolving this. Please reopen if
it's still an issue.

Oh, I was not aware of that bug and disabled S/MIME by default in the current
development version.

I'll make the default depending on the Outlook version.

Emanuel tested this. As I wrote, inline editors are another thing.

Should be fixed in git master. There is a small issue that sending encrypted
drafts from the inline reply window does not work. But if you open the draft in
a composer the Sign / Encrypt state is the same as it was when saving the draft.

The inline thingy is another issue. I can catch that and add a Messagebox to
tell the user she should open the messagecomposer to send.

More difficult then I thought.

For PGP/Inline this should currently work. I had the problem that I can't
manipulate the Body in MAPI but over Outlook in the write event this worked.

PGP/Clearsigned support i've disabled for now.

With regards to mime mails:

I could modify / restore the mail there already using old code. The message
is not formed correctly but this looks like just a bug in the revert code.

As it turns out this was totally an understatement ;-) The old revert code can't
have worked. Maybe for S/MIME under some circumstances but otherwise not.

The problem is the main part how Outlook builds the MIME message. Were we have
very limited control about it. Just removing our attachments and leaving the
original MIME attachment leads to a MIME structure like:

<quote>

This is a multipart message in MIME format.

------=_NextPart_000_0000_01D12C53.76E82C90
Content-Type: multipart/alternative;
boundary="----=_NextPart_001_0001_01D12C53.76E82C90"

------=_NextPart_001_0001_01D12C53.76E82C90
Content-Type: text/plain;
charset="iso-8859-1"
Content-Transfer-Encoding: 7bit

------=_NextPart_001_0001_01D12C53.76E82C90
Content-Type: text/html;
protocol="application/pgp-encrypted";
boundary="nextPart3167407.zD7nylcVYN";
charset="iso-8859-1"
Content-Transfer-Encoding: quoted-printable

<!DOCTYPE HTML PUBLIC "-W3CDTD HTML 3.2//EN">
<HTML>
<HEAD>
<META HTTP-EQUIV=3D"Content-Type" CONTENT=3D"text/html; =
charset=3Diso-8859-1">
<META NAME=3D"Generator" CONTENT=3D"MS Exchange Server version =
rmj.rmm.rup.rpr">
<TITLE></TITLE>
</HEAD>
<BODY>
<!-- Converted from text/rtf format -->
<BR>

</BODY>
</HTML>
------=_NextPart_001_0001_01D12C53.76E82C90--

------=_NextPart_000_0000_01D12C53.76E82C90
Content-Type: application/pgp-encrypted;
name="Unbenannte Anlage 00001.dat"
Content-Transfer-Encoding: 7bit
Content-Disposition: attachment;
filename="Unbenannte Anlage 00001.dat"

Version: 1
------=_NextPart_000_0000_01D12C53.76E82C90
Content-Type: application/octet-stream;
name="msg.asc"
Content-Transfer-Encoding: 7bit
Content-Disposition: attachment;
filename="msg.asc"

-----BEGIN PGP MESSAGE-----
Version: GnuPG v2

hQEMAx7U8Lxs+8kSAQf/eB4zBTz/VSVBBI+ihh/PSorJ98BRh5earBqF8HjmGZce

<end quote>

This is nothing even an MUA like KMail can handle. And GpgOL can handle this
neither. So if we modify the message we have to do it somehow in a way that
Outlook builds a Mime structure again that users can work with.

As we can actually send MIME messages I looked at the code in mimemaker that
builds a message. Using some tricks from there I was able to recreate a PGP/MIME
mail. But this needs special handling for all our message classes.

Still too buggy to commit. Leaks plaintext and I have at least seen that it led
to a duplicated message once.

Modifying the mail in the afterwrite event did not work good. While the
attachment changes were synced to the server Outlook itself didn't reparse the
mail correctly. This let to a weird out of sync situation between MAPI and OOM.
But testing looks like this could work from the Write event indeed. Which would
be even better because we only have one write and we could replace the "Wipe
Message" code completely by just reverting the mail back to the original.

I'm optimistic this can be done. :-)

It's a bit iffy though and might be especially annoying from a performance side
for exchange users. Still it will be better then the Status Quo because you can
still use the mails with other clients.

The trick is not to revert back the message in the Write event, as we have to
work on the OOM in the Write event but in the AfterWrite event where we can work
on MAPI.

I could modify / restore the mail there already using old code. The message is
not formed correctly but this looks like just a bug in the revert code.

This is fixed in master. Kleopatra / GPA is now started on demand. E.g. The
first time a crypo operation actually happens. This also means that GpgOL is
more robust if the user shuts down Kleopatra.

The first crypto operation might take a bit longer but this is better then to
increase the startup time even if a user does not plan to use crypto in this
session. And if we fix T2136 this will hurt even less :-)

Clarified title.

We've added support for Outlook 2016 with gpg4win 2.3.0 (gpgol 1.3.0). Which has
just been released two days ago :-)
Please try this version.

I had a look at your logs. Indeed I can see where it crashes, and it really
looks like gpgol did something at the time of the crash. It crashed after a Mail
was Loaded by outlook and before it was read. I've read the related code again
and could not find a problem.

If you are testing again anyway Please set your EnableDebug value to 1536. This
enables Debug output related to outlooks internal data model and could help.

It was a crash. Outlook has been terminated and restartet automatically (can be
seen in gpgol log).
Now I'm going to start with gpgol enabled and I'll enable all other plugins step
by step.

We don't see any more crashes in testing and we had some other people test
1.3.0. before the release. Is it crashing or does outlook freeze up / not
responding?

Just to ensure that we have comparible setups, have you enabled other plugins
again? If so which?

I'll take a look at your debug output to see if I find something out of the
ordinary.

I installed the new gpg4win 2.3.0 release and activated gpgol. When answering an
email I had another crash reported in ntdll.dll. But I suspect that the crash is
related to gpgol even though it's not directly reported.
Now I'm going to leave gpgol disabled.
The corresponding logs are appended and might be that there are some hints inside.
Best regards
KJ

After installing the lastest beta I had unfortunately several crashes of Outlook.
The crashes are reported for severeal modules. There was no crash in module
gpgol reported, nevertheless I disabled gpgol.
If there are some news - even no more crash - I'll give an update here.

Best regards
KJ

I had all flags enabled (2047) and set it now to 1.

Thanks again.
KJ

There was only a crash at the very beginning when I started outlook and forwared
an email with encryption to myself. Outlook crashed but module MSPTLS.DLL has
been reported to be the cause of the failure.

I'll try it out.

In the log file of gpgol I noticed that there is a huge amount of messages
in.lock taken or released and the same for out.lock. Is it possible to disable
selectively these lines because it floods the disk and I'd like to have some
debug lines enabled if some problem might occur.

Yes just set the enableDebug registry setting of GPGOL
(HKEY_CURRENT_CUSER/Software/GNU/GpgOL) to 1
You currently probably have it at a much higher level.
This will disable the most spamming debug outputs and leave the important stuff
active.

Thanks for the quick fix and your detailed answer.

I installed the new version and had nearly no problems: I successfully exported
contacts serveral times (even waiting more than 10 minutes) and de- and
encrypted emails multiple times.

There was only a crash at the very beginning when I started outlook and forwared
an email with encryption to myself. Outlook crashed but module MSPTLS.DLL has
been reported to be the cause of the failure.

In the log file of gpgol I noticed that there is a huge amount of messages
in.lock taken or released and the same for out.lock. Is it possible to disable
selectively these lines because it floods the disk and I'd like to have some
debug lines enabled if some problem might occur.

Best regards
KJ

I think that I found and fixed the problem.

There is a method COM addins have to implement to indicate weather or not it's
Ok for them to be unloaded. I totally forgot about that method as I've
implemented it years ago as part of the standard "stuff you have to implement
for COM".
This method used bad values to check if an unload is ok (which basically should
be never as long as we are not deactivated).

My current understanding is that the trigger here was that after exporting
contacts some internal cleanup code in Outlook checks if there are Addons that
are no longer needed and unloads them if they tell Outlook that this is Ok.
Which we dit. So Outlook unloaded us and any more calls to GpgOL crashed.

I could confirm with debug output that this was called right before GpgOL was
unloaded and we told Outlook that it's Ok to unload us.

This cleanup can probably happen under other circumstances, which would also
explain the random crashes you've seen before.

Thanks again for your patience and your excellent feedback in this issue which
made it possible to find and fix this.

The fix is:
http://git.gnupg.org/cgi-bin/gitweb.cgi?p=gpgol.git;a=commit;h=1362563c9370cc9c00463293a7f6eeb91b9424de

A binary with the fix is:
https://files.gpg4win.org/Beta/gpgol/1.3.0-beta108/gpgol.dll

There will be a gpg4win release with this Version soon.

Please let me know if you are still seeing crashes ;-) I could not reproduce any
more crashes with this version.

As a workaround it's possible to disabled gpgol before exporting contacts.
After enabling gpgol it's possible to decrypt/verify encrypted mails without
problems.

I can confirm the behaviour related to time. When gpgol is enabled before
exporting contacts and then disabled I can do this multiple times (for at least
twice). When waited for some time gpgol is unloaded as soon as the "Fertig
stellen" has been clicked, which means beginning the export.
That's really weird...

I understand whats happening here now. I still don't undestand the Why.
For my tests I've disabled all other Addons to rule out interference.

In the crashing case Outlook unloads GpgOL from it's memory. This happens
regularly with the test described in T1837 (aheinecke on Nov 16 2015, 08:07 PM / Roundup). But as the original Report
mentioned crashes at other points I'm not really sure what causes this but
Exporting contacts seems to be a good trigger.

This Unload does not call any of the Registered Cleanup methods like
"OnDisconnect" etc. and GpgOL is never Unregistered in Outlook. The only thing I
can see is that DLLMain is called with "PROCESS_DETACH". And that ProcessExlorer
no longer shows GpgOL as loaded.

Any callback outlook calls into gpgol, getCustomUI, ApplicationEvents ItemLoad
etc. will cause a crash as the memory behind those callbacks is invalid. This is
why we've seen crashes apperantly all over the place.

Ok now that we know the What. We have to figure out the Why. A websearch about
this has not brought up anything.

My current speculation is that there is some interference with out old
ExchangeExtensionCode that might be activated by exporting contacts (this dialog
looks really old).

Well but at least we are getting closer. In fact in my development version I
have a nice messagebox popup "Gpgol was unloaded Outlook will now crash" :-) But
yeah thats not really helpful...

While Werner mentioned that he might have solved this in previous versions I'm
not seeing this in the code. I'll have to test with GPA as it might be that
progress information causes gpgol to temporarily yield the event loop.

Tested this and GPA also blocks Outlook the same way as Kleo. Which was expected
as the blocking happens in GpgOL.

I was able to reproduce this five times. It appears that time is also a factor
here. When I start GpgOL look at a mail, go to contacts ands export them I dont
get crashes.

But when I wait ~10 minutes after opening the contacts view I get the crashes
pretty reliably.

Funny thing is and I see from your logs that something similar happened at least
once for you that the last Debugoutput of GpgOL is way before the crash.

e.g.

• switch to contacts at 18:30
• wait 10 minutes
• export contacts, switch to mail.
• Crash.

Last debug output before the crash is from 18:30 eventlog shows the crash at
18:40 and the restart of gpgol and the startup procedure is logged at 18:40.

But the ItemLoad event where the EventLog says gpgol is crashing is what gpgol
should be getting once we switch back from the contacts view to the mail view.
But gpgol does not get it. I've added debug output in the first line of that
function and it is not called.
The handler for the ItemLoad event is also not deleted and still valid.

Next step will be for me to look at the address of GpgOL's event handler
function and at the address which is called when outlook crashes... I still
don't even have a theory what's happening here.

But I'm happy that you are able to reproduce crash.
Good luck for debugging.

Regards
KJ

Datei->Optionen->Erweitert->Exportieren->In Datei exortieren->Weiter->Outlook
Datendatei (.pst)->Weiter->Weiter->specify file name for the export->Fertig
Stellen->OK.

\o/ This way I was able to reproduce the crash after switching back to the Inbox
and Outlook complained that GpgOL caused the crash.

Wow. This will be fun to debug, we are doing absoluetly nothing with contacts.

forgot the file

Yes that's true, when disabled, all works fine.

In Outlook's folder tree view I select "Kontakte" and then
Datei->Optionen->Erweitert->Exportieren->In Datei exortieren->Weiter->Outlook
Datendatei (.pst)->Weiter->Weiter->specify file name for the export->Fertig
Stellen->OK.
If gpgol is active then Outlook usually crashes at that point or when changing
to the inbox.

I just replay the scenario enabling gpgol and susequently exporting contacts and
it worked - see latest Application view entries and last gpgol debug output.
In the file appended there are the application log entries since Nov. 13th
(Source: Outlook and "Application Error") and the relating gpgol log file if active.

Outlook is exchange based and connected to an AD.

Best regards
KJ

Just to recap:

• You can export Contacts with GpgOL disabled.
• When you have GpgOL enabled Exporting contacts Crashes Outlook.

How do you export contacts? I've tried with selecting "Personen (probably
Persons)" tab and dragged & dropped my contacts to a folder in the filesystem.
.msg Files for those contacts are created and no crash. I can switch back to
Mails, decrypt mails etc. no crashes for me :-/

This is with outlook 2013 and 2016 and either with or without an Exchange
Account. (But exchange without Active Directory)

Can you again send me a log of such a crash please? Maybe with all the added
debug output I can see something out of the ordinary.

Just a short update. Working with addin-options dialog now works fine with beta104.
But as soon as I'm exporting contacts Outlook crashes again.
Best regards
KJ

Thanks for your notes. gpgol beta 104 now loads again.

Ah and with regards to the mime-send variant. That is a variant of GpgOL that
has experimental support to send PGP/MIME mails. (e.g. Mails that follow a
proper standard for crypto mails and are more interoperable with thunderbird and
gpgmail)

Then you won't have to encrypt the body anymore and add encrypted attachments
etc. but rather you just mark "this mail should be encrypted" and when you send
it it will be encrypted including all attachments etc.

Once we release 1.3.0 this will be the basis for the next version for now we
mainly use it for internal testing and as a proof of concept. The UI is not
where we want it to be. I'll write something about it in the wiki.

Btw. I've tried to explain a bit how the MIME Support in 1.3.0 works in the wiki
already: https://wiki.gnupg.org/GpgOL/MIMESupport

Ah and with regards to the mime-send variant. That is a variant of GpgOL that
has experimental support to send PGP/MIME mails. (e.g. Mails that follow a
proper standard for crypto mails and are more interoperable with thunderbird and
gpgmail)

Then you won't have to encrypt the body anymore and add encrypted attachments
etc. but rather you just mark "this mail should be encrypted" and when you send
it it will be encrypted including all attachments etc.

Once we release 1.3.0 this will be the basis for the next version for now we
mainly use it for internal testing and as a proof of concept. The UI is not
where we want it to be. I'll write something about it in the wiki.

Btw. I've tried to explain a bit how the MIME Support in 1.3.0 works in the wiki
already: https://wiki.gnupg.org/GpgOL/MIMESupport

A change I did for the 64 bit version of Outlook caused the load problem. This
did not happen for my development builds as they were not run cleanly (in
contrast to the builds I upload)

Fixed with https://files.gpg4win.org/Beta/gpgol/1.3.0-beta104/

Apologies and thanks for your feedback!