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PC browser/I haven't tested it in the app.
It's been years and this is still an issue, for which I'm using an external fetcher and randomiser.
If you have a playlist with lots of songs (I assume it would happen a lot more with music than videos), the randomiser will only play and loop the first hundred tracks or so. Any newly added content is not played, and the playlist comes to an end far too early while not playing all the songs.