using SMIME and PGP together: error "unusable secret key"

OK, made some tests.

If I use SMIME+PGP private keys together and made the setting “automatic sending”, than PGP is used. Would be nice to add a setting that I can decide which of both techniques should be used.

If I delete the private PGP key in Kleopatra and use automatic sending, a error message “unusable secret key” appears. I have to close Outlook and start it again. Then it works.

If I use SMIME+PGP private keys together and made the setting “automatic sending”, than PGP is used. Would be nice to add a setting that I can decide which of both techniques should be used.

The algorithm is that it first tries to find valid signing keys and valid recipient keys for OpenPGP. If they can’t be resolved it falls back to S/MIME.

If I understand you correctly you would prefer it if it was the other way around → prefer S/MIME. While I doubt that many users will want that I can see that it might make sense in some usecases. Should not be much work. I’ve opened a Ticket for this. ⚓ T3961 GpgOL: Add option to prefer S/MIME over OpenPGP in autoresolution (Btw. feel free to also use dev.gnupg.org)

If I delete the private PGP key in Kleopatra and use automatic sending, a error message “unusable secret key” appears. I have to close Outlook and start it again. Then it works.

Yeah. Checking for Keys is an expensive (slow) call. (It’s what happens during the “Resolving Recipients” stage). So we keep an internal cache in GpgOL that checks for Keys when an address is first used and then caches the information. This leads to the “super quick” encryptions without any dialog (except the pinentry).

I don’t really see a case for deleting keys in the day to day use but we could handle this case more gracefully. Task is: ⚓ T3962 GpgOL: Switch to external resolver when encryption with internal resolution fails

Hi Andre,

many thanks for your reply and your efforts!

Best wishes,
Zigg