Under Kleopatra -> Settings -> Configure Kleopatra -> GnuPG System -> In the Tab Secret Keys -> Is there either "Delete unused Passwords after N Seconds or Delete Passwords after N Seconds set to zero or the option "Do not use the password cache for signing" set? In this case this would be normal and expected behavior because it turns of the caching.

Maybe it's due to the fact that I used a non-admin installation? Actually I'm also surprised that it worked that way. What kind of debug logs could I supply?

For me with Gpg4win 4.2.0 it works as expected, that is all UIDs which have a checkmark are certified in one go, entry of password only once. Used the key given in description for the test.

Eva and me tested this using our 2.2.42 release candidate on Linux and
on Windows and were not able to replicate your problem.

@raysatiro: Please re-open if you are able to give us a reproducer

There is a utility named kbxutil which can be sued to dump the pubring.kbx file without any post-processing by gpg. I would check whether there are any other keys after the VideoLAN key. iirc, kbxutil ist not commonly installed; you may need to build the software yourself or copy the pubring.kbx to Linux and check it here.

We have not seen this problem anymore in recent versions. Thus closing.

Might be a TOR Thing?

As long as we can't replicate this, it does not make sense to keep this bug open. Please re-open it if you run into it again in a replicatable way.

Thanks fro the report. Unfortunately I am not able to reproduce this on our systems. It might be an issue with other software on your system or a problem in our code. This is the first such report and as long as we don't get reports from other users, we can't do much for you. Please try installing on a different system or if you can provide more information feel free to re-open this bug report.