I have not seen this. But I suspect that it would be fixed if our encryption no longer causes Outlook to become "unresponsive". I'm already working on this for T3509 and have a development version which already does the encryption in a way that the pinentry / key resolution are just a modal dialog over outlook and no longer block the GUI of Outlook completely.

1. Collect all data in OOM, then start a thread to do the encryption.
2. Do a proof of concept that this actually works and outlook lets us do it with our usual window message async handling.
3. Update my Keyresolver patches in Libkleo and build a "libkleo-tool" to do the key resolving.
4. Figure out Window Management / Create a Qt Overlay over the Mail window to block it from closing while encryption happens. This will resolve all bugs related to window mangement of the current key resolution.

From your log I can see that the verification fails with "Unsupported Protocol" which is weird in itself. But at least with the fixes for T3538 (they are included already in your version) it should then show the unverified body. So this is a second problem. I tried to reproduce this for sent mails but even if deliberately break them they are displayed correctly.

Hi Andre, thanks for your help.

I can understand your reasoning, it makes sense.

We are always looking for ways to improve the messaging but the idea here was no keep it as simple as possible.

Depends: Not everything you see has been protected by the signature. Thus such a description would need to go into more detail.

The fix was released with Gpg4win-3.0.3

as your behavior is unusual please verify that no other Addons interfere, we are still trying to figure out if there are incompatible other addons. So please try to disable any other addons and try again.

No more reports of this since 3.0.2. With 3.0.3 I fixed an additional memleak which should further improve this. Resolved for now.

Multiple confirmations -> Resolved.

With git bisect I tracked it down to a0326ffb755c4a49a259cea3d83831d9ede7d5d9

Hi @aheinecke
Its also german:

GpgOL should use the same language detection code that GnuPG also uses. If you open a command line (cmd) and run "gpg" in that command line is it also in german?

I've noticed that myself and the cause for this is the code which we use to ensure that the key resolution dialog of Kleopatra opens in the foreground.

Thanks again for the test, your patience and the report :-)

:-)
I can confirm, that 2.0.6-beta14 is working and until now, Outlook did not crash :-)
Great work, thanks!

Ok so I found out that you could even trigger this bug without persistent options just by activating and deactivating any S/MIME option on a mail. This somehow changed the behavior of Outlook.

I can also confirm that 2.0.6-beta9 fixes my issue with this too. Also with my own exchange server!

In T3656#109404, @aheinecke wrote:

But that's it.
With these Options set and explicitly unchecking Sign & Encrypt before sending I get the exact same behavior that you two describe. Mails are sent unencrypted.

But that's it.
With these Options set and explicitly unchecking Sign & Encrypt before sending I get the exact same behavior that you two describe. Mails are sent unencrypted.

In T3656#109402, @JHohmann wrote:

Yes, I also have this option enabled:

And no, I disable Signing and Encryption, before enabling PGP Encryption for the specific email

Yes, I also have this option enabled:

I have now also the error T3662
Will try also 2.0.6-beta9

In T3656#109394, @Mak wrote:

Ahh, and yes I use a public personal s/mime cert to sign my mails. nothing else.

OK, found the problem now. Its the smime settings. I have set them to sign all outgoing mails. And thats where the problem starts...

Ahh, and yes I use a public personal s/mime cert to sign my mails. nothing else.

My too, no outgoing rules.

I do not have any rules configured that are applying to outgoing mails. (As far as I can see them with a non-administrative account)
Are there any group-policies, that might affect the behavior of Outlook regarding to GpgOL?

Another question: Any outgoing Filters (Email Rules)?

@JHohmann Your log is similar in that I can see two Write events after the send of which there should only be one. Somehow we seem to do crypto on a copy mail object and another mail is acutally sent.

I don't think that it is possible to create you an account.

Quoted Text

Any chance that I could get a temporary test account on your Server?

We have the same problem.
Sent emails are not encrypted with gpg4win 3.0.2
Outlook 2016
Exchange 2010
Locale: German
Plugins: Skype, OneNote, Sophos

I can confirm that this appears to be fixed in 2.0.6-beta9.

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

I've changed the behavior now so that PGP/Inline also works with Exchange Online.

In T3656#109246, @Mak wrote:

I sent it to a user on a different Mailserver. On my setup its nothing special... Win 10 Enterprise N en, Office 365 Pro Plus en, Kaspersky Internet Security. Server Win 2012 R2 with Exchange Server 2013 and GFI Mailessentials.
I don't think there is anything special... :-(

I sent it to a user on a different Mailserver. On my setup its nothing special... Win 10 Enterprise N en, Office 365 Pro Plus en, Kaspersky Internet Security. Server Win 2012 R2 with Exchange Server 2013 and GFI Mailessentials.
I don't think there is anything special... :-(

As this is still waiting for info for two years and I can't reproduce with current GpgOL -> Resolved.

This is strange, something in your setup must be different from other users. Any Idea what might be special for you? In your log it looks like only the send event for the encrypted mail is passed.
Where do you send your mails to, to another user on the same exchange server?

I can confirm that PGP/MIME works ok for me.

I disabled all my add-ins and tested it again. Still the same. Mails are sent unencrypted.
Tried also to send a plain text message

I can reproduce the issue but only for PGP/Inline, encrypted only mails. PGP/MIME works finde. This allows for an easy workaround (sending PGP MIME) so Prio down to Normal.

All e-mails I tried to open with 2.0.6-beta7 gpgol.dll were readable and showed the correct content in my environment, now. Great!

While trying to reproduce another bug I've set up an account with Exchange Online. With that account I had similar behavior with empty mails shown. The behavior also matched to the logging of the last mail in your log.

Prio High as this makes GpgOL unusable in such a setup.

I give this high priority as sending unencrypted is pretty much a worst case scenario. :-o

Enabled Logging, and here the results with some Errors inside...

As answered in the forum: https://wald.intevation.org/forum/forum.php?thread_id=1837&forum_id=21&group_id=11 :

Unsupported Protocol means that GpgOL can't find your GnuPG installation. Maybe something went wrong during the install of Gpg4win?

Hi @hs,
given that you have used the instructions from the link above to look at the message,
I'll take it that you are using an IMAP/SMTP setup for mail transportation?

A signed but not encrypted message appears in the same way (visible in Sent, empty in Inbox)

Looking at the messages from above using another PC, same Windows 7 and Outlook 2010 but Gpg4Win 2.3.3 :

• received message in Inbox is decrypted shown correctly inline both in preview and opening it
• original message in Sent is not decrypted, but shown as encrypted with gpgolXXX.dat attachment

Hence, it shows the opposite behavior to the 3.0.2 handling.

One problem seems to be that the content of Inbox message differs from this one in the Sent folder (10 vs. 20 KB).
The content of the Inbox is shown as empty, even using the "show source" option. Saving the message as plain text shows a PGP part inside, but this is ignored by Outlook.
I tried this advice:
How to view the message source in Outlook
But the result is the same, after maked as read, the message becomes unreadable.

• fresh install of Gpg4Win 3.0.2
• reboot
• openening Outlook 2010 with only one plugin (GpgOL)
• sending an encrypted email to myself
• trying to open that email (no content)

@aheinecke Because it was mentioned in another comment, I've tried to restart Outlook with the GpgOl plugin enabled, only. Same result. But the fact that I could see the message just after arrival, but not in a second approach may point in a direction that incoming messages are processed by an server-based filter changing potentially vulnerable email content (as embedded links).
I could try to log the complete process of sending an email to myself, decrypting once and failing in a second trail. This would actually increase the size of the log file.

@hs Your log is interesting but I don't yet understand it. We see a "Load" event for an encrypted mail, create our internal data modelling. But later there is a mismatch between the reference Outlook gives us and our internal reference (Failed to find mail in map).
Out of the blue there might be something I could do in that case but it's still somewhat unclear to me why this state occurs.

Just installed Gpg4Win 3.0.2.
Had a very similar effect with Windows 7 / Outlook 2010:

• Sending an encrypted e-mail to myself.
• E-mail will be decypted once after receiving.
• After that, e-mail is shown as "unsecure" and with empty message body (both in preview and own window).
• E-mail in "Sent" folder still decryptable with right content.

I've added gpgol.log for opening Outlook again after receiving the e-mail (with empy body, now).

Correct, this was also the case before, sorry for the misunderstanding.

The HTML in the body below the text on the GpgOL-1.4 side is a known issue of GpgOL-1.x we only added proper HTML handling with GpgOL 2.
GpgOL before 2.0 just appended the text/html mime part to the text/plain mimepart in multipart/alternative mails.

PS: And I can confirm that I have a lot of HTML Garbage in my mail body (on the receiver plain text side):

I can confirm that it works for me, too: Fantastic, thanks!

In my tests it's fixed with: b8276a4f3acecee2e467c0530007aedc9db5936a the plain text body now uses similar code to the html part. Makes sense anyway. The difference was mostly historic as GpgOL before 2.0 did not handle HTML parts at all.

If I send "Nur Text" (plaintext only) under formatting it works as expected. We query Outlook for the Body from the MAPI Data model and just get the wrong value returned. For the HTML part we use the Outlook Object Model (as we had a similar problem there that the MAPI data was not updated properly.)
The fix is obvious. We can use similar code to our handling of the HTML body. This is a workaround for an Outlook bug IMO, why should sending from drafts differ from the usual sending *sigh*

Wow, fast reaction! I'm happy to help evaluate a possible fix for this.

I can reproduce that problem and have opened T3614 for this.

Hi, first of all I want to report back that with beta15 that the following issues did NOT arise anymore, fantastic!

I only installed 3.0.2 this morning so this hasn't had much of a chance to happen.