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:

There are more Logfiles:

Are those mails sent by GpgOL with Outlook or recieved? Can you explain your complete Workflow and state what software was used in it?

Can you relate to the issue described in the GPG4win Forums?

You could try to use NO-MIME (or PGP/INLINE) instead of the OpenPGP/MIME standard. You can change the way of packaging your encrypted content in the GpgOL Addin Options.

Confirmed. Same behaviour and environment as described by HB1000 but with Windows 8.1 x64.
Outlook displays a message inside the mail "decrypting message..." (something like that) and then the message window is blanc as if there is no content.

Do you have any idea about this issue?
Exactly same behaviour here.
Windows 7 Enterprise 64-Bit, Outlook 2010 (Version 14.0.7188.5002, 32-Bit), GpgOL 2.0.1
Tell me if you need any diagnostic logs, ...

I'm also facing the same issue here.

Oh, God, someone please solve this problem. It is so annoying. Tried everything I could, installed and uninstalled the softwares and accomplished nothing.

i'm facing the same problem. Would love to see this problem solved

I'm also facing the same issue here.

I’m facing this issue too..

That seems to be a conflict between the two extensions. We need to look deeper into that so learn why it could go wrong and whether there is a way to work around the conflicts.

If someone could help me on how to debug on outlook, I could produce more information about this bug.

See T3441 for one additional screenshot with error codes.

The log file shows that gpgex (or explorer) crashes.

The output from gpgsm -K in the last quote is perfectly okay. -K works by iterating over all public keys and checking for each public key whether the private key part is also available. If the private key is not available gpg-agent returns an error.

This doesn't seem just to affect E-Mails but also File-Encryption.

I'm trying to find all relevant information first, then we can discuss who should work on this.

So, who is going to work on this?

I recieved the Log File of a user which may helps analyzing this problem further

I think it was a version problem.
I have now installed gpgOL (2.0.1) and gpg4win version 3
It's working.
Just that emails do not directly access "decrypt", but those that are sent from MAC arrive as an attachment, with ASC termination. I need to change the extension to PGP, decrypt, and generate a file without extension. Then I need to change the extension to EML and then I'll be fine.
Can you fix it?

I assume you installed gpg4win. Which version did you install? 3.0 is the latest.

@aheinecke is completely right. I just copied from Outlook's "show source".

We now explicitly delete the body instead of relying on the fact that the Outlook MAPI to MIME conversion deletes the body. Somehow this worked in the past but no longer does. I could not bisect it as 1.4.0 showed the same problem but old test mails from July 2016 did not show the problem. Newer ones from August 2016 already showed it in the sent mails folder.

I think this is a duplicate of T2416 please let me know if you still see the crash with the current beta / release candidate of gpg4win-3.0

This is fixed now with ef038f2d1db15ef14c238137c1c42a99bbe25f42 initially we only took the first attachment. Now we check for the position of the created MOSS attachment. This explains why a second try worked because the MOSS was already created.

This is what you get if you "show source" in Outlook so it's only the headers.

Is that really the entire mail? I can see only the header of the mail but not the body. How did you copy the raw mail?

Talked with Jochen and tested this. Jochen's test forwarded the mail so he ran into T2854

I can't reproduce this issue. I've imported the attached mail with KMail and synced the folder to outlook.
GpgOL did decrypt the mail. It did not set the category correctly (These were two other bugs which I've fixed now) and displayed the wrong status information but decryption happened.

Outlook 2003 is no longer maintained.

I think its done and released with beta-270

There is highlighting now but we don't have the fancy new keyresolver.

No. But as of 3.0 GpgOL for Outlook 2003 and 2007 is no longer maintained and the support for this will be removed in some future version. This bug only affects new installations of GpgOL on the unmaintained (by Microsoft) Outlook 2003 and Outlook 2007 Versions. So -> Wontfix.

Should be resolved. Reopen if it is still an issue.

@aheinecke did you change the default?

Ok this looks nice already. My plan is the following:

Andre merged this already.