I completely agree, Tailscale will not just solve your issues. If you want to have is as simple as possible for your users you are going to need to expose it publicly for your users. And the reason I posted the comment above is to share a solution that has worked for me to get my users "Smart"TVs to work. Honestly if someone where to make a service that provides a “plex networking” solution for jellyfin I think allot of people would consider using it and leave plex for good!

Yeah then this might not be a great idea for you, unless you have the possibility to fix a machine if you visit. But I want to make it clear this is not a fix all thing just trying to help :D

That doesn’t slove the problem if your Smart TV doesn’t support tailscale or something like Wireguard. Using another machine connected to a VPN like for example Tailscale/Headscale and then using ssh portforwarding allows you to access the service(jellyfin) on the device without support.

It would be like this:

Jellyfin <-- Tailscale/Headscale <— Machine forwarding the jellyfins port <-- Smart TV

This can be done with a command like this:

ssh -L 0.0.0.0:8096:jellyfin_tailnet_ip:8096 -f -N user@machine

If you have a machine at her place that is on most of the time you can have tailscale on that device and then make it ssh into itself with ssh portforwarding on!

Edit: You can also selfhost headscale and do the same as the comment below said

I have done what you are looking for on OPNsense. And I’m pretty sure it can also be done with OpenWRT.

You will need to setup multi WAN and setup some static routes and use your RoadWarrior setup.

Aka you want this:

Phone › Via Wireguard › OpenWRT › Via Wireguard › VPN provider

I don’t have a guide on how to do it but I will try to find one and update this comment if I do. But here are some Guides that might help you in creating it!

Multi WAN Guide

MullvadVPNs OpenWRT Guide for Wireguard (Should work with other providers)

OpenWRT Wireguard Guides

I’m also including the guide to setup Roadwarrior & External VPN provider for OPNsense so you can get a idea of how it should be done and work

OPNsense guide I used to create my Wireguard WAN

OPNsense guide I also used for Wireguard WAN

OPNsense Guide I used for my Roadwarior Setup