this post was submitted on 05 Jan 2024
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You're not doing anything wrong, the playlist function is just half-baked. My guess is they put just enough work into it to intend for it to be used in small chunks, such as a single evening.
Edit: I've just seen your clarifying statement, and although Plex playlist is relatively non functional I've never seen that specific behavior. Try hitting play on an item in the playlist instead, that works for me.