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You may have found this answer or another one by now but a simple way to achieve this (as long as you don't want to use the shuffle function) is to manually create a playlist and add each song multiple times. Example (.m3u playlist in same directory as music): #EXTM3U a.mp3 a.mp3 a.mp3 a.mp3 b.mp3 b.mp3 b.mp3 b.mp3 c.mp3 c.mp3 c.mp3 c.mp3

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