I retested this with the current beta and It works without problems. I somehow suspect that the permanent access loop from Kleopatra caused other Smartcard operations to be canceled. Since the test setup is not really good to reproduce to for Ebo I resolved this myself.

This is very much unrelated to any GnuPG code so I can say this is resolved for Gpg4win, too.

because I did not test with gpg4win yet. And I'm not familiar enough with the code base to say that it does not need to be testet with 2.4 again. Feel free to close it and move to done in the gpgcom workboard if you think its resolved for good.

So why not resolved?

For me it is like if you open a save file dialog. You want it to remember where you saved a file the last time you saved it. But if you just browse around and cancel it, it should not store that location.

We don't change settings. We just remember what the user used the last time. That we save this information in the same file as settings doesn't make them settings. (It might be more correct to save last used keys/options in the state file where window sizes are saved since some time to better separate this information from actual settings.)

In T6584#179021, @ebo wrote:

(It takes maybe 10 second before the file disappears when you hit F5 in the explorer)

Works with VS-Desktop-3.1.90.277-Beta

Reopened as I noticed that the last testmail had an empty body in my sent folder. And I am sure that I wrote some text. Please check.

But I wonder if we should not address https://dev.gnupg.org/T6683#176429, the text there is not changes in this Beta version.

In GnuPG-VS-Desktop-3.1.90.267-Beta-Standard it works, aside from T6805:
You do not get the new "no x509" message wrongly any more even when quickly sending a mail after restart of Outlook.
But it correctly appeares if no X509 is available.
And the message is configurable via the registry setting HKLM/HKCU \Software\GNU\GpgOL\smimeNoCertSigErr (although I do not know how to add line breaks there, but that is not important).