Shuffle Won't Stay on in iTunes

When I try to turn shuffle on in iTunes, it will not stay. Even if I have it on right before, (option says "turn off shuffle") right when I hit "play" in iTunes, it plays the very first song, and it has turned shuffle off. (option says "turn on shuffle"). It works fine on my iPod. I have tried restarted iTunes and I have restarted my computer, neither of which solved the problem. Ideas? Not a huge deal, I suppose, as I can turn it on during the first song, but I'd rather have it work from the beginning and stay on. I'm running iTunes 11.2.2.3 on Windows Vista. (Yeah, yeah. I know. Vista works just fine for me and I'm happy with it, and I really don't want to upgrade to Windows 8 or get a new laptop.)

I'm having the same problem after installing the 3.0 software update. My playlists will not shuffle, the same song just keeps playing. I went into the settings/iPod and turned off 'shake to shuffle' but it didn't change anything. I have a set of earbuds with a control on the cord that will allow me shuffle to the next song but it's a pain in the a$$ when out on my bike and such.

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As I said, some items cannot be purchased with an existing credit on an account no matter how much it is. It can only be purchased with a charge to a credit card.

Shuffle Won't Stay on in iTunes

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