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.

I think I fixed your problem. We had a similar problem in the past and the fix there was not to invalidate the UI (Update GpgOL's status button) so quickly when the selection changed.

According to our tests and the Message board this is fixed.

Thanks for that assessment.

What happens in the log:

I can't reproduce I sent myself serveral messages in which i pasted a PGP Message and they worked. I tried both HTML and Text plain messages.
To be sure I also installed Gpg4win 2.3.0 and sent myself a message with that and that also worked :-/

Thank you for your detailed report and the description for the reproducable setup! We will investigate in that issue!

I've sent an email from Outlook using version 2.3.3, to myself. What I see in Outlook with version 3.0.1 is:

-----BEGIN PGP MESSAGE-----
Version: GnuPG v2
hQEMA6jFcgdYY5bVAQgAhWTqExXJVk3aPC5rKYFUeb0NSR+TtChjBzxBrFzQ5qDr
trJiT6o7XoFYDKwdJFXMv81Zcetsu/dOq3dPoCpaQDAtna8xshJDogsx7bOV5bvO
9kLzegZqUk4RzAJLCOTkIISh/Qi6o6kXL4+Iwm17FKfVb0MSAjmrOV50SevrKpD+
PxEYr7BJHRwA9HcYMCb1tvao74AFShZV2olEuwuGvF2nuuqTl6MngKI0Qhteds3F
B6MPOckhHvOCLr3u1z7ld+svggaVFhPyTbXuGxTXAHyieeUr0yf+p4UufdTj3XTn
L/ZeK7l0TKJykbWZmFfZFDClyEDvQx1Vq7ggLuIbh9I/Ab/LkshjC+QGFmfpVaH/
D03ZQv+RStnlI3ZVWvWsAxsaWp/hEsP4RHkmVQXhI4YeRBw1e6TeXzvTvMidjnBC
=oLiX
-----END PGP MESSAGE-----

In the GpgOL ribbon the button shows a question mark and an "unsafe" label.

We both came from Gpg4win 2.3.2, WE BOTH upgraded to 3.0, as a consequence WE BOTH were unable to decrypt mails once encrypted with Gpg4win 2.3.2 (and actually way older Version of Gpg4win): Please also see https://wald.intevation.org/forum/forum.php?thread_id=1781&forum_id=21&group_id=11 for further description of the issue. Now I AM able to decrypt these mails, my collegue is not (even she also is on 3.0.1).

So to get this straigt:

Unfortunately not, since I am able to decrypt them now (also encrypted with GPG4Win 2.3.2) AFTER the upgrade from 3.0 to 3.0.1 (we both went from 2.3.2 to 3.0 to 3.0.1).

In T3419#106033, @cdeibert wrote:

Hi, VERY odd: My collegue has the exact same installation and environment (actually software deployment-based), she still is suffering to decrypt Mail encrypted with GPG4Win 2.3.2.

Hi, VERY odd: My collegue has the exact same installation and environment (actually software deployment-based), she still is suffering to decrypt Mail encrypted with GPG4Win 2.3.2.

In T3367#106015, @RockyMM wrote:

Treat this as "Cannot Reproduce".

In T3419#105989, @hs wrote:

Just installed Version 3.0.1. From a first glimpse, it seems to work more stable in Outlook context.
But decrypting older plain text messages still fails.

Hi, also installed 3.0.1. For me decrypting older plain text messages now works!

I really want to retest this, but I cannot promise anything. We are using a workaround regarding encrypting email.

Thanks for that clarification Jochen; at least it confirms I'm not going mad. I've got it installed now so will update this if it happens again although, in the meantime, it might be taking a look at the log I attached (if you haven't already) to see if it hints at any behaviour that you know has been fixed.

by "just released" I mean: minutes before i wrote that comment. Since you mentioned gpg4win 3.0.0 in your post, I think you worked with the now old stable release.

Just installed Version 3.0.1. From a first glimpse, it seems to work more stable in Outlook context.
But decrypting older plain text messages still fails.
Using GPA (copying PGP ASCII text into dashboard) decrypts contents without error.
-----BEGIN PGP MESSAGE-----
Version: GnuPG v2
...
-----END PGP MESSAGE-----

Updated this morning and just had a freeze again. Enabled debug mode now. For me the freeze often happens when my pc is locked and I'm not using it for a while, then return to my PC and select another email.

When you say "just was released", do you know what time that was at? My reason for asking is that I checked for an update just before posting this bug report! I'll try it and see how it goes.

This error doesn't seem to appear anymore in Version 3.0.1 and it doesn't exist anymore for me.

@cosimo193 ; gpg4win 3.0.1 just was released. May you check if this error still exists with that new version?

@RockyMM Does this issue still persist with the newer Versions of Gpg4win, like 3.0.1?

@cdeibert, can you may check if this error still exists with the freshly released Version 3.0.1 of Gpg4win?

Hey @pkoevesdi, Gpg4win Version 3.0.1 was just released. Can you may download and install it and check if this issue still exists?

Version 3.0.1 just hitted. @madjari - may you can check if the various bugfixes in that version fixed your issue as well?

With the Release of Gpg4win 3.0.1 the Error doesn't appear anymore while testing with Windows 10 (64bit) with Outlook 2016 and Windows 7 (64bit) with Outlook 2010.

rO13950a985228 Works around this problem by launching Kleopatra in the background when Outlook is started.
This should both speed up the first operation and work around this issue. In my opinion it's better to waste some resources in the background if Kleo is not needed then to create a bad user experience if encryption does not work and results in a hang of outlook.

I could not reproduce it again on Friday. Did some code staring to find the issue but failed. Everything looks Ok.

Forgot to mention this bug in the commit addressing this. ( 278893850ed926d4646929ee97576a8d09fd4998 )

Thanks for your reports.
I can finally reproduce this on a new Test VM which I gave little resources. Most of the time it does not work. Sometimes it works. Looks like a timing issue, on my main development VM which is fairly quick it always works. I'll work on it.

I am connected via IMAP. Sometimes Outlook also crashes when I handle a message that is in a local inbox not directly associated with an account. It may be relevant that I have two IMAP accounts configured that run on different key pairs and all messages are shifted to a local inbox on arrival.

This was only for multipart/alternative HTML mails which was a fairly recent feature for GpgOL.
The encoding for html mails was handled incorrectly as it took the encoding of the text/plain part and not the text/html part. Fixed now.

Indeed. Thanks for your report I can reproduce this. Funny how this was missed through all the Beta's and pre release testing.

How are you connected to your server? I mean IMAP, or Exchange MAPI or is it a Hotmai / Outlook.com account?

I resolve this. If it is not displayed anymore it means that outlook should handle it.

Tested with Gpg4win-3.0.0-beta17 with GpgOL-2.0.2-beta8 on Windows 10 (64bit) with Outlook 2016.

I enabled the error and did the following with Gpg4win-3.0.0-beta17 with GpgOL-2.0.2-beta8 on Windows 7 (64bit) with Outlook 2010

In T3442#105339, @aheinecke wrote:

In T3442#104402, @JochenSaalfeld wrote:

1. Mails encrypted with S/MIME are stored with "No Data" in the sent EMail folder, but arrive properly at the recipients (you will recieve a readable copy, if you add yourself to the list of recipients). This Issue breaks the GpgOL Plugin after some time which is leading to the described Problem.

Fixed with 474cc15d8e331c9def298dbbfe3b99e6c8cf8035

Versions Used: Gpg4win-3.0.0-beta17 with GpgOL-2.0.2-beta8 on Windows 10 (64bit) with Outlook 2016.

@tstreibl thanks for helping with your feedback!
Please note that this issue (T3442) still has the status "testing", because we want to perform some more tests before declaring it resolved. :)

In T3442#105466, @tstreibl wrote:

Starting Outlook still bring up the "Fehler in der Benutzeroberfläche von XML von "GpgOL .....Unbekannte Office.Steuerelemente-ID: TabComposerTool" Message Box.

Sorry for my inpatience...but it's a little bit hard to understand why the above, very simple test procedure obviously isn't reproducible on your systems.

Starting Outlook still bring up the "Fehler in der Benutzeroberfläche von XML von "GpgOL .....Unbekannte Office.Steuerelemente-ID: TabComposerTool" Message Box.

tested your new .dll. Created a new email. Choosed "sign". Pasted an email adress from outlook address book into the "an" field. Outlook crashs. Took me 2 seconds to test. What the hell are you testing?

Thank you very much. Both the signed only and the encrypted mail are fully valid for me (checked on the IMAP server and with kmail) and don't contain any references to gpgolXXX.dat. This means they were correctly converted to valid PGP/MIME Mails.

Dear Andre

This means that the MAPI to MIME conversion did not happen.

Jochen could you please test this on one of our test VM's again and resolve this then?

A new binary for GpgOL can be found under: http://files.gpg4win.org/Beta/gpgol/2.0.2-beta8/ or for http://files.gpg4win.org/Beta/gpgol/2.0.2-beta8_x64/

@aheinecke Regarding closing: I'd say that we should have a test on this one and then close it for only the refocussed "send-folder problem".
Can you provide an updated gpgol.dll drop in replacement?
Some of the users in the forum may be willing to test as well.

In T3442#104402, @JochenSaalfeld wrote:

1. Mails encrypted with S/MIME are stored with "No Data" in the sent EMail folder, but arrive properly at the recipients (you will recieve a readable copy, if you add yourself to the list of recipients). This Issue breaks the GpgOL Plugin after some time which is leading to the described Problem.

Jochen can you please confirm that this works reliable for you too?

This indeed is a mixup of the protocol detection and likely a regression from a fix for exchange support. (On Exchange emails from exchange to exchange look the same as sent mails as both don't go through the MIME conversion)

This error looks like an element might be referenced that is not available in Outlook 2010. In that case the problem should be reproducible for users that have Developer Options -> Show Add-In Errors enabled.

When receiving an S/MIME mail that is encrypted, the successful log looks like:

Comparing the gpgol.log files in the case of OpenPGP decryption (successful) and S/MIME decryption in send folder (failing).

Here is the link to the wald report by John Mrkva:
https://wald.intevation.org/forum/forum.php?thread_id=1785&forum_id=21&group_id=11

Same here: I can confirm the bug. I can move an email, if i unselect it before an then use its context menu to move it.
This behaviour is already mentioned in the readme:
c:\Program Files (x86)\Gpg4win\share\gpg4win\README.en.txt

Yesterday I could reproduce that emails in the "send" folder cannot be decrypted anymore.

This week I'm trying to make progress with this issue.

Confirmed, this is the exact same problem!

I tried to melt it down to a specific beta release with which it isn't possible anymore to decrypt send emails.

Since this is a bug that is related to two different parts of the gpg4win package, this bug now only cares about the GpgOL Issue, that GpgOL crashes and cant decrypt messages from the sent folder that are encrypted with S/MIME. All File Based Issues are belonging to Kleopatra are documentet in the KDE Phabricator (https://phabricator.kde.org/T7310).

1. Mails encrypted with S/MIME are stored with "No Data" in the sent EMail folder, but arrive properly at the recipients (you will recieve a readable copy, if you add yourself to the list of recipients). This Issue breaks the GpgOL Plugin after some time which is leading to the described Problem.

2. Files that are Signed and Encrypted to a S/MIME Certificate is broken. When you select a file and encrypt and sign it to a recipient, only a detached signature will be created and the Encrpyted file is missing. (Very similar to Issue 1, but file based).

https://phabricator.kde.org/D8368

There is just another person experiencing the same problem with an Exchange based account on Win10pro x64, Outlook 2016 x86.

I don't have access to this description. I used official, newest releases. I searched for this issue on the web, on the gpg4win page but did not find a solution. Is there any accessible information?

So far we could recreate the following issues: