Selfhosted
A place to share alternatives to popular online services that can be self-hosted without giving up privacy or locking you into a service you don't control.
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When you "cast" from the phone to the Chromecast, what happens it that the phone gives the Chromecast an URL where it can find the stream to play. The phone can read that stream because it's connected to the Tailscale VPN. The Chromecast isn't, so the stream URL is inaccessible to it. You see the Jellyfin logo because that's a feature of casting (the app on the phone gives the Chromecast a logo to show).
There's no point in announcing the subnet from your laptop, because your laptop is not a router for the local LAN. You can use this to reach local LAN devices from remote Tailscale nodes but not the other way around.
Some possible solutions:
I use this same method to stream to Chromecast regularly (with Kodi). I will sometimes have issues with some encodings, or desyncs when pausing, but it is solid enough to support streaming full movies at 4K.
For 3, if router supports it could also try doing static route via Tailscale joined machine that has IP forwarding enabled
This is not necessarily true. It's almost always possible to use the 2.4GHz band on one side and the 5GHz one on the other and multiple networks on one WiFi interface isn't impossible either.
Modern Android devices can provide hotspot of the connected WiFi without any modifications. For some anecdata: My FP4 with LineageOS 20 and a Samsung A50 (Android 11) can both do it.