On gpg4win-5.0.0-beta330 everything works fine again (both smime and openpgp regardless of expiration).

I now imported all certs in testzertifikate_2023/ (smime and openpgp) and generated a new one (openpgp, default settings, expiration 2028) and still get no valid signing certs in okular

added gpgsm log:

Ingo mentioned some maybe related expiration year 2038+ ticket, but I only found one for kleo: https://dev.gnupg.org/T7069

Issue about no valid smime certs found on signing split into: https://dev.gnupg.org/T7697

3 non-hang logs, all took ~20s to open the file (with 20s "Keine Rückmeldung" shown in Okular)

The problem with the invalid certificates seems to be unrelated. Isn't there already a ticket for Okular for certificates which expire after 2038?

If keyboxd sometimes takes 6 seconds, then I'm not surprised that stuff times out after 8 seconds occasionally. Or well. we need more numbers to determine that.

And in the first case, about 6 seconds are lost starting keyboxd:

2025-06-23 13:16:55 gpgsm[3252] DBG: chan_0x000000000000022c <- VERIFY
2025-06-23 13:16:57 gpgsm[3252] Kein aktiver keyboxd - `C:\\Program Files\\GnuPG\\bin\\keyboxd.exe' wird gestartet
2025-06-23 13:16:59 gpgsm[3252] Warte bis der Keyboxd bereit ist ... (8s)
2025-06-23 13:17:01 gpgsm[3252] DBG: chan_0x0000000000000260 <- # Home: C:\Users\g10\AppData\Roaming\gnupg
2025-06-23 13:17:01 gpgsm[3252] DBG: chan_0x0000000000000260 <- # Config: [none]
2025-06-23 13:17:01 gpgsm[3252] DBG: chan_0x0000000000000260 <- OK Keyboxd 2.5.6 at your service, process 4748

Here's the gpgsm debug log:

The keylisting hangs ticket for Kleopatra: T6623

In T7658#202206, @svuorela wrote:

@ikloecker is https://git.gnupg.org/cgi-bin/gitweb.cgi?p=gpgme.git;a=commitdiff;h=f23cef6f66a44c5c1cc8717f74b658d14fde04e5 needed to be forward ported to split gpgmepp ?

@ikloecker is https://git.gnupg.org/cgi-bin/gitweb.cgi?p=gpgme.git;a=commitdiff;h=f23cef6f66a44c5c1cc8717f74b658d14fde04e5 needed to be forward ported to split gpgmepp ?

It could be connected to those "keylists hangs" problems. On Kleopatra it took some time to refresh the key list. After that I can open the signed file again.

Well, now I also can reproduce the hanging on verification again (opening of an unsigned document is fine, of a signed document hangs).
Maybe the signing part above is important to trigger it - although it happened now in a clean state after a reboot, so it should not be caused by e.g. leftover processes.

I'm quite sure, that I used a fresh install on a new VM, but on another fresh one I can't reproduce the verification part anymore and the signature is shown as valid.

The only time I succeded in reproducing this was when I broke my gnupg setup and got a mix between gpg from one version and gpg-agent from another.

In T7658#201260, @TobiasFella wrote:

That screenshot is for kleopatra crashing, not related to okular.

That screenshot is for kleopatra crashing, not related to okular.

We have updated patches for long in the gpg4win repo and thus I close this bug.

We investigated this a bit and it only happens when trying to sign with a non VSD key when gnupg is in VSD mode

Something went wrong during signing - the question is what.

This is still an issue. Since the double click opens a registry entry the working directory of Okular is Windows. Since it is the working directory of the explorer so that is unusable, but it should still be able to somehow take the location from the actually opened file and use that for a save file suggestion.

This works for me

should this go into the upcomming VSD release?

Existing file. I downloaded a pdf into the local Download folder of my Windows-VM and worked with that.

Is the document loaded from an existing file on disk or directly as a url from a remote server? http(s) or windows share ?