My playlist won
My playlist won't shuffle on mac. The music stops after each song
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Since Music will not advance to an unchecked song, the symptom you are seeing usually means that your songs have become unchecked.
If you don't see the checkboxes at all, put the list in View > As Songs, and also enable Preferences > General > Show Songs List Checkboxes.
if you need to recheck a bunch at once, hold the Command key and click any empty checkbox.
if you are running a European version, the checkboxes are called tick boxes. :-)