SOLVED: Windows + Caddy + DuckDNS - how do I setup SSL?

[TheDreadPirate]

If you go to port 8096 you are bypassing Caddy. Port 8096 is Jellyfin's http port. When you omit the port, just about all browsers will default to https on port 443, which is the port Caddy listens on. When going through Caddy on port 443 that is when the connection is encrypted.

Further more, you should NOT be port forwarding 8096 to avoid the possibility of remote connections going directly to Jellyfin unencrypted http port. You do not need to port forward since Caddy will be handling external connections. And you do not need to port forward for local clients to be able to access port 8096.

Additionally, you do not need to port forward port 80. This, again, avoids the possibility of unencrypted external connections. Caddy does not need the port for certificate requests.