I’ve had this issue for a few months, trying to cast live TV to both my Chromecast 2gen, and to my Nest Home Mini, but I eventually figured it out.
What has fixed this issue for me, was to go into the server settings, and uncheck the following two options…
Use hardware acceleration when available
Use hardware-accelerated video encoding
Now, instead of getting an error, I can cast live TV to these devices. However, I have since noticed that these devices are playing a transcoded stream, instead of directly playing/streaming it from my server.
I’m also noting that since there is no hardware acceleration support for my server, (no Intel GPU) I don’t understand why the server would rather give an error, instead of gracefully falling into a mode that the Chromecast can support. I think it’s either a developer oversight on Plex’s end, or a Chromecast device issue.
I must disclose, that my server version is still at 1.19.4.2935 as I’ve had issues with 1.20.1.3252 crashing on me, when trying to transcode video from remote. That was before I figured out my issue with casting to Chromecast devices. (is it related somehow?) I’ll try upgrading my server again tomorrow, leaving those hardware acceleration settings off, and seeing what happens.