Some people don't realize that rolling 1,2,3,4,5,6 on a die in order is as likely as 6,4,1,2,5,3 even though the second set of outcomes might seem more likely because it looks more random. Mlodinow explains that most people really don't understand randomness, and a 'truly random' playlist might have the same song twice in a row, play a few songs from the same album in the normal order, and things like that.

If I remember correctly, his explanation was something along the lines of this: a truly random playlist is not desirable to most users, which challenges the claim 'I do believe the ordering is truly random the first time it's generated' in the top answer. If you do, please include some additional information about the situation, including whether you receive any error messages (and what those are), and what happened when you tried the above steps.Leonard Mlodinow touches on this issue in The Drunkard's Walk. If your music doesn't play when shuffle is off, or if the issue continues after trying the above steps, don't hesitate to respond back.

Check to see if you can play your music in another user account: How to test an issue in another user account on your Mac - Apple Support.

Check to see if shuffle works in safe mode: Use safe mode to isolate issues with your Mac - Apple Support.

After the computer is back on, open iTunes while holding the shift key on your keyboard. Then, restart your Mac by clicking the Apple  menu and selecting 'Restart.' from the drop down. Quit iTunes by pressing Command+Q or clicking iTunes > Quit iTunes from the Apple  menu.

If so, try the following steps, testing after each: I'm happy to help!įirst, I would recommend checking that the other music in your library will play if shuffle is off. From your post, I understand that when shuffling your library in iTunes, only songs recently imported to iTunes will play, even after toggling shuffle off and back on. Thanks for stopping by the Apple Support Communities.

New itunes shuffle songs