Right? It’s like a trust fall. You just have to cross your fingers and hope for the best.

I updated my Dietpi setup today, because a new version was available. It went very well, and everything works perfectly after a reboot.

Tailscale creates a new virtual network, and anything you want to connect to the Jellyfin server needs to be in that Tailscale network. You need to hook up the Roku device to Tailscale. I have never owned one, so I can’t say anything about that. But maybe that’s what you should figure out next.