I just found out, that Drafts are not S/MIME encrypted, if

• draft encryption is activated and set to a S/MIME cert
• S/MIME is enabled
• S/MIME is not prefered

Note: I also activated Sign/Encrypt by default, if that matters

Same behavior (on vsd-3.3.3-beta90.12 @ win10) for smime encrypted mails:

Looks good to me on vsd-3.3.3-beta90.12 @ win10:

Looks good to me on vsd-3.3.3-beta90.12 @ win10 (temporary filename is now attachment.odt or e.g. attachment (002).odt)

Debug log for vsd:

Also still present on vsd-3.3.3-beta90.12 @ win10 (mail is not moved)

Using gpg4win-5.0.0-beta369 @ win10 I can't reproduce it with use-keyboxd, but without use-keyboxd:

Current logs for a forever hang:

still reproducible on gpg4win-5.0.0-beta369 @ win10

In T6117#205379, @ikloecker wrote:

I guess this is a typo because the CSR looks like an encryption-only certificate.

Sorry, I just found out, that windows caps the filename earlier than max length, so my former tests were invalid.

All mails touched by gpgol should already have a GPGOL_UID_DASL. So to replicate:

1. Send a new encrypted mail (e.g. Edward -> Ted)
2. Don't open that mail, but open the context menu: Move -> Other Folder ...
3. Select a subfolder of INBOX and click OK -> the mail is not moved

Looks good to me on gpg4win-5.0.0-beta369 @ win10

Looks good to me on gpg4win-5.0.0-beta369 @ win10

Still the same behavior as described in https://dev.gnupg.org/T7240#202915 on gpg4win-5.0.0-beta369 @ win10

Looks good to me on gpg4win-5.0.0-beta369 @ win10:

Looks good to me on gpg4win-5.0.0-beta369 @ win10:

Note: If i set an invalid path in "Software\\GnuPG:Install Directory"

• the gpgconf -X output does not change
• the self-test Config File 'libkleopatrarc' fails with Error in archive definition tar: 'pack-command-openpgp' empty or not found

This probably can only be tested with signed releases?

Current state in gpg4win-5.0.0-beta369 @ win10:

Looks good to me on gpg4win-5.0.0-beta369 @ win10:

Notepad  window
Text to process  edit  Either enter a text you want to sign or encrypt, or an encrypted or signed text you want to decrypt or verify. You can also enter certificates in text form to import them.  blank
t
e
s
t
Signing and encrypting notepad...
Successfully encrypted and signed the notepad

Looks good to me on gpg4win-5.0.0-beta369 @ win10

Looks good to me on gpg4win-5.0.0-beta369 @ win10 (no lines omitted or duplicate readings):

pinentry-qt  dialog  Enter passphrase
Passphrase:  edit  protected  blank
[...]
does not match - try again  dialog
OK  button  Enter

Looks good to me on gpg4win-5.0.0-beta369 @ win10

Looks good to me on gpg4win-5.0.0-beta369 @ win10:

PGP
GPG
P7M
P7S

Tested on gpg4win-5.0.0-beta369 @ win10.

Current state in gpg4win-5.0.0-beta369 @ win10:

Looks good to me on gpg4win-5.0.0-beta369 @ win10.
Can't reproduce it anymore, message is S/MIME decrypted instantly:

Looks good to me on gpg4win-5.0.0-beta369 @ win10: The dialog with the progress bar is showing up instantly now.

Looks good to me on gpg4win-5.0.0-beta369 @ win10:

Here are the messages and logs, when trying to open them:

Key Approval dialog used by GpgOL (VSD only) looks good to me on gpg4win-5.0.0-beta357, Outlook LTSC Standard 2024 @ win10 (compliance mode):

How to test this? The follwing happens for an attachment of an encrypted mail on gpg4win-5.0.0-beta357, Outlook LTSC Standard 2024 @ win10:

Moving an encrypted message on Gpg4win-5.0.0-beta357, Outlook LTSC Standard 2024 @ win10 into an inbox subfolder of Ted.Tester and back works for me, too. Does this confirm, that it's working now?

Looks good to me on GnuPG-VS-Desktop-3.3.90.8-Beta-Standard.msi (3.3.3 betaversion) @ win10
(tested with 10 restarts)

Mostly looks good to me on GnuPG-VS-Desktop-3.3.90.8-Beta-Standard.msi (3.3.3 betaversion) @ win10

Looks good to me on GnuPG-VS-Desktop-3.3.90.8-Beta-Standard.msi (3.3.3 betaversion) @ win10

nr.1
nr.2
schwarz
weiß

Looks good to me on GnuPG-VS-Desktop-3.3.90.8-Beta-Standard.msi (3.3.3 betaversion) @ win10

Looks good to me on gpg4win-5.0.0-beta357 @ win10 for the following migrations (as stated in the description):

• gpg4win 4.3.1 -> gpg4win 5.0
• gpg4win 4.4.1 -> gpg4win 5.0

Looks good to me on gpg4win-5.0.0-beta357 @ win10.

Looks good to me on gpg4win-5.0.0-beta357 @ win10:

I created a new issue for the "Keine Daten" error: T7768

Looks good to me on gpg4win-5.0.0-beta357 @ win10

Looks good to me on gpg4win-5.0.0-beta357 @ win10:

Regarding the "Keine Daten" on corrupted message: the diagnistics says e.g.: "gpg: Prüfsummenfehler; c83745 - f75c60"

Looks good to me on gpg4win-5.0.0-beta345 @ win10

Looks good to me on gpg4win-5.0.0-beta345 @ win10

Looks good to me on gpg4win-5.0.0-beta345 @ win10

Looks good to me on gpg4win-5.0.0-beta345 @ win10

Looks good to me on gpg4win-5.0.0-beta345 @ win10

Looks good to me on gpg4win-5.0.0-beta345 @ win10

On gpg4win-5.0.0-beta345 @ win10 the progress bar is shown:

Ah, i missed the description edit. Then it looks good to me.

Looks good to me on gpg4win-5.0.0-beta345 @ win10

seems not to be included in gpg4win-5.0.0-beta345 yet

commands with -v

Ok, it was a missing update (although windows claimed to be up-to-date).
After installing 2025-06 [...] KB5060829 the Microsoft Print to PDF feature is available again and printing also works in Kleopatra/Okular.

It's also the same error in Okular, when a pdf is printed.

Same on gpg4win-4.4.1 @ win11 (here a bit more debugview context)

3	3.503991	8584	kleopatra.exe	org.kde.pim.kleopatra: Paperkey export finished:  0 status:  QProcess::NormalExit
4	3.691599	8584	kleopatra.exe	QPrintDialog: Cannot be used on non-native printers
5	3.691981	8584	kleopatra.exe	QPrintDialog: Cannot be used on non-native printers
6	3.692752	8584	kleopatra.exe	org.kde.pim.kleopatra: Printing aborted.