Autofill doesn't fill all the way?

Hello, I have a quick question that I hope can be resolved easily. When I autofill my 2nd gen shuffle from my full music list (much more than the shuffle can actually hold), it doesn't fill up all the way. I don't get an error message. It just stops, and hitting autofill again does nothing. From there, I can only manually add songs to the playlist. Is there something I can do to fix this?
Thanks!

Try restoring the iPod, that does sounds like a Software issue on the iPod.
http://docs.info.apple.com/article.html?artnum=300701
Also make sure that you are running the latest version of itunes. 7.0.2

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