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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Stick with the VPN. No point in exposing more services with possible security vulnerabilities.
I love Jellyfin but I would absolutely not make it accessible over the public internet. A VPN is the way to go.
Yeah I'm thinking maybe just have family sign up for tailscale.
Why not just run your own WireGuard instance? I have a pivpn vm for it and it works great. You could also just put jellyfin behind a TLS terminating reverse proxy.
Sounds like a pain to get non technical family members to use. If you're willing to break the non web app you could always put it behind an authenticating proxy (which is what I do for myself outside of VPN, setting up a VPN on a phone is obnoxious and I only look at metadata anyway on my phone)
CGNAT is a big reason.
Or headscale, works like a charm