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After the recent plex player debacle I'm once again trying to come up with a way for me and my diaspora to share media using Jellyfin, but without relying on Tailscale. We have several media libraries, and some of the library hosters are not too tech savvy, so coming up with a solution to replace the ease-of-use of plex hasn't been easy.
What's wrong with tailscale?
Hey, I did the same. It’s not as bad as it seems. Get yourself a domain name from cloudflare and use it. I got mine for $10 a year. Then just installed cloudflare on my Debian server and all that (I’m sure you know the rest) then made users on my admin jellyfin dashboard and started sending people their usernames and passwords. The only difference for them is now they would need to enter the server URL on the first page of whatever they use then username and password. Good thing these jellyfin clients have the page of entering the server URL in your face with their “connect to server” button. Let me know if you have any questions.
Careful with using CF Tunnels for streaming content. It's against their ToS to use the free tier for streaming content, so they can technically turn it off whenever they want from my understanding.
From what I understand, if you turn off caching you aren’t violating their TOS. I’ve been doing this for about 2 years now and have yet to have anything happen. Multiple friends use my Jellyfin server daily.