Am Freitag 11 November 2022 14:40:13 schrieb Angel de Vicente:
> I actually have no problems signing with S/MIME also inside Emacs (as
> far as the passphrase has been cached). And I have no problems signing
> with PGP (pinentry loopback works fine then).
>
> So it looks like something that affects exclusively pinentry loopback
> while signing with S/MIME

As always, there must be a difference in how OpenPGP and S/MIME 
signing with GnuPG is called from Emacs/Gnus.
(There is a small chance that it is with the specific keypair you are using.)

Comparing detailed logs of OpenPGP and S/MIME might reveal the difference.
I darkly remember Gnus using GPGME, if this is the case, maybe a GPGME_DEBUG
log can help you. Otherwise you need to look into how Emacs can produce more 
details about what it is going (I am not an Emacs user, so I cannot really 
help you there.)

Regards
Bernhard

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