Cannot get caddy working at all, no conections go through

[TheDreadPirate]

Most of our apps will cycle through various port and protocol combinations if the provided URL doesn't work.

http+8096
http+80
https+8920
https+443

"https://jellyfin.domain.tld", with no port specified, should first try port 443, the default https port that caddy should be listening on, before trying 8920. "http://jellyfin.domain.tld" should try port 80 first before trying port 80.

And, no, browsers do not try other ports. That would be a security issue.

The error you are getting SOUNDS like you are typing in "https://jellyfin.domain.tld:8096". Don't do that. Just type in "https://jellyfin.domain.tld". Caddy handles forwarding it to port 8096 internally.