I am in my iTunes library (not a playlist) and have "shuffle" turned on (songs, not albums). If I click on "play", it plays the song currently highlighted, then stops (it does not play another song afterwards).

The only way I get it to play several songs is by manually checking the songs I want to be played. Which obviously is the opposite of random shuffling.

Also, when I turn off shuffle, then turn it on again, I don't see any change in the order of songs in the library (whereas when I'm in a playlist, I do see a change in the order).

In all the help forums, I've only found answers to the question of how to turn "shuffle" on. I know that. But how do I get iTunes to play songs randomly once shuffle is turned on?

  • 1
    What version of iTunes? What platform? This is not the behavior I get when I perform these steps in iTunes 10.5.3 on my Mac.
    – Daniel
    Commented Mar 11, 2012 at 23:02
  • 1
    What about iTunes DJ?
    – segiddins
    Commented Mar 11, 2012 at 23:22
  • iTunes shuffles once on the song you first select, but if you select anything again it won't reshuffle. Also, is it possible that you don't have Repeat All on for your main library? (the settings can be different between playlists) Lastly, the main library doesn't shuffle, only playlists do. Commented Mar 11, 2012 at 23:45
  • @LucasDerraughhe Tracks don't visibly move around, but it does shuffle play.
    – Tuesday
    Commented Mar 12, 2012 at 0:34
  • @Daniel L: I have 10.5.3 on iMac OS X 10.7.3
    – Ralph
    Commented Mar 12, 2012 at 18:05

2 Answers 2


When iTunes shuffles through a playlist, library, or other list, it only will shuffle among items for which the "checkbox" column is checked. By default, this would include all the items in your library; only if you uncheck the box for a song would that remove it from the list of songs to shuffle.

It sounds as though your library is set up with all the songs unchecked. If no songs are checked to be included in shuffle, one gets the behavior you describe. The solution is to go to your library and make sure all your items are checked, not unchecked.

  • No, all the songs are CHECKED in my library. It is exactly the same as normal. Shuffle is turned on, and nothing is happeneing. I have the same problem. I turn it on and off again, and the order stays the same. This has nothing to do with the 'checkbox'
    – Ralph
    Commented Dec 11, 2012 at 3:40

My version of iTunes did the same and I was finding it very tricky to get it to randomly shuffle through all my tracks, even though they were all checked.

Strangely, it's now working fine again. All I had to do was switch to the "songs" view of my library, hit CTRL+A (to highlight all songs) & press play. That seems to have kicked things back off. Now even if I clear the "Up Next" playlist and close iTunes, next time I open it up I just have to press "Play" and it will randomly shuffle over all my checked songs.

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