did you set up letsencrypt/certbot in the first place to write files to /usr/local/etc/letsencrypt/live/domain.org/cert.pem
? If so, did you take care to replace domain.org
by the actual domain you are using?
The documentation you linked looks a bit funny in that the first command writes to private key/cert to privkey.pem and cert.pem, but then the second command tries to read in a (likely) certbot-created certificate. I guess if you followed the steps you need to replace usr/local/etc/letsencrypt/live/domain.org/cert.pem
in the second command by the cert.pem created in the first one?
Either that (if you want to use a self-signed cert) or point it at the certbot-created files in /etc? If I understand the jellyfin docs correctly, the second command just translates the usual .pem files into a .pfx file for jellyfin, so should work with any certificate you give to it.
If you’re going to do the latter, you should also add a certbot deploy script to regenerate the .pfx file after a certificate renewel (and possibly restart jellyfin, idk).