Selfhosted
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What? I’m confused by the question the OP asked if it’s just automatically that way.
OP uses tailscale to connect to everything and not his local connection.
Which is really weird IMO.
If you want to run everything over a VPN, you're going to have issues when the internet goes out. Use VPN as a fallback or to get around CGNAT, not as a primary way of routing everything.
Here's my setup:
So when I connect on my LAN, my router just points the domain to the machine running Jellyfin and I get all the goodness of TLS. When I connect outside my LAN, my VPS tunnels TLS through the WireGuard VPN to get around CGNAT and I get all the goodness of TLS. So it doesn't matter where I connect, I use the same URL and get TLS.