How do I get Shuffle to work on my iPod Touch?

Sometimes Shuffle works for my music and other times it keeps repeating the same song.  I have tried hitting "Shuffle," tried resetting the iPod.  Nothing seems to help!  It usually happens after an update to the operating system.

Connect the iPod to the computer and go to thesSummary pane for the iPod in iTunes and click on update. Se:
iTunes: Backing up, updating, and restoring your iPhone, iPad, or iPod touch software
Also see:
iOS 5: Updating your device to iOS 5

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