Casting sessions have to come from a player unfortunately. The server doesn’t inherently cast. You could in theory dedicate some kind of linux docker on the plex server to act as a permanent client, but that would be custom end to end.
Ah, makes sense. Home Assistant’s integration must have a player component built in to allow it to cast media via their integration… is there a DLNA-type binding that could work on OpenHAB? Open to any suggestions to get a playlist going (the lack of the Chromecast providing a notification is the problem I’m trying to solve). Right now, I just have my media in the sounds folder of openHAB and stream locally.