this post was submitted on 19 Sep 2025
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Can you explain to my mom how to install tailscale on her Roku and that she has to turn it on each time she wants to use Jellyfin but then back off again when she wants to watch something on a different app?
Why exactly would they ever need to turn VPN off again? It’s not like all their traffic will go through it if it’s on, unless you specifically configure stuff that way (exit node, routes).
And one option to do the VPN stuff is on their router too, so it’s totally transparent to them. More stuff to configure though, unless running owrt or some other router software compatible with Tailscale.
As far as I understand, Tailscale (being a Wireguard network) doesn't need you to flip it off and on - if you're connecting to the relevant endpoint it gets routed through that, otherwise it just goes the normal way.
Not gonna pretend that means the setup is trivial to nomies, but you could probably set it up for them and not have to worry about it.
Yeah but it doesn't auto connect on a lot of devices. So if you restart the device you have to reconnect. Tech illiterate people struggle with this concept.
Have zero knowledge of Roku but for example with AppleTV boxes it is totally fire and forget, Tailscale is always on in the background and apps will find my media servers through it.
And I’ve noticed even tech illiterate people will learn to become literate when there is some motivation, like a huge movie archive :) Flipping a preference like VPN on if they want to use certain app is certainly within realm of possibility.