Selfhosted
A place to share alternatives to popular online services that can be self-hosted without giving up privacy or locking you into a service you don't control.
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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.