Get your elderly mother an Apple TV and infuse, then connect with Tailscale. It’s pretty friggin’ smooth in daily operation. Apple TV’s UI is no easier to get lost in than Roku, and actually has fewer pitfalls if you toggle one setting (the one that makes one home tap open the Apple TV app, and a second press while in that app actually go home, by default; switch that to always go home on any press of that button no matter what)

I dunno if Tailscale works on Roku but otherwise that would indeed be entirely viable too, last I saw Jellyfin’s app on there is really good. Likely need a server powerful enough to transcode, though, lots of (all?) Roku devices don’t have hardware decoding for newer codecs like h.265. That’s one big benefit of an Apple TV, it can hardware decode damn near everything.

I use Jellyfin and when it works it’s great but a few small things make it totally unusable for a non-technical family member.

One thing is when it can’t see the server it doesn’t just say it can’t see it, it acts like the issue is you’re not logged in and then when you log in (having to type your password manually each time, on a TV) it then fails.

This is only really diagnosable if you can access both the client and server and is a complete failure and very tedious experience if you only have client access.

Feels like I experience this at least once a month so couldn’t ever set this up for family members remotely.

I set my dad up with a Linux box as a daily driver for him - he keeps the desktop on , and the roku jellyfin now has a clean proxy into jellyfin over the tailscale network. Giving him a desktop I can remote into was a great decision that paid dividends for him :)

You can point Tailscale toward a $5 exit-node VPS and Caddy/nginx through a cheapo-but-memorable-domain to get a Jellyfin Dashboard up in a browser. I assume running the domain and port through the Jellyfin Roku app would work fine (can't be sure as I've never used a Roku).

Just mind your ACLs