I recently setup Jellyfin on an Ubuntu box at home. I wanted to use SSL certs and Tailscale for the web interface.

You’ll need to create a cert in pfx/pkcs12 format

Replace the servername with yours I put mine in a script

#!/bin/bash
cd /root
/usr/bin/tailscale cert server.example-example.ts.net
openssl pkcs12 -export -inkey /root/server.example-example.ts.net.key  -in /root/server.example-example.ts.net.crt  -out /etc/jellyfin/server.example-example.ts.net.pfx  -passout pass:
chmod 755 /etc/jellyfin/server.example-example.ts.net.pfx
service jellyfin restart

Then enable https Enable https

Once you’ve verirfied everything works you can force https Require https