FWIW: The fix rO75f46829054e is part of GpgOL since 2.6.3

Tested with VS-Desktop-3.3.90.12-Beta

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

I can't find any causes of slowness in keyboxd initialization. I think that there is a situation where it simply takes time on Windows.

As there has been no more feedback on this for years, I'll close this.

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

what ever was fixed with the attached commit we can not test.

I see no workaround.
The attachments in the original mail are not gone, yes.
But the mail can't be forwarded with them.

Tested with VS-Desktop-3.3.90.12-Beta, GpgOL 6.5 (WIN10 and WIN11)

2.2 test can be done with GnuPG-VS-Desktop-3.3.90.12-Beta-Standard.msi from Sep 17

Test with 3.3.90.12-Beta:
The test mail from before does not cause a spawn cycle and no high CPU load any more. (Tested without "show as text only", as it was not relevant before.)

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)

Interesting. That means to replace hundreds of scripts in an average organization :-(.

@ametzler1 Thank you.

Some data points:
The latest version of the standard (issue 8) has "The -a and -o binary primaries and the '(' and ')' operators have been removed." instead of "obsoleted" https://pubs.opengroup.org/onlinepubs/9799919799/utilities/test.html

After a discussion we decided to drop the idea to save the status of the check boxes even for only the box "encrypt for others".

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.

test -a is not a POSIX construct, I intentionally avoided it.