I do have port 80 open as well as 443, both going to my Jellyfin HTTP/HTTPS ports respectively. HTTP seems to work for both when I access “pretty” domain and the FreeDNS URLs directly. It’s really only when I try to force HTTPS that I’m having issues.

I’ll play around with Let’s Encrypt today to see if I can get the FreeDNS cert applied. I’ve tried to use AI to assist me in learning how to do all this, it suggests I need both my “pretty” domain and the FreDNS domain tied to the same Cert, which Im unable to do at my current domain registrar, so I might also need to move that but I’ll take it one step at a time.