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Recently, I've noticed that when I hit shuffle play on my largest playlist of just under 3000 songs, only the top 100 or so will be shuffled.
For example, if I organise my playlist by recently added, only the more recent songs will be queued. If I organise it by title, only songs beginning with a number or the letter A will play in the queue.
It's a total joke! Shuffle should pick songs at random from the entire playlist, not just from a tiny proportion of it.