Last played updates wrong songs on shuffle, but updates nothing in iTunes

I recently upgraded from a 2nd to a 3rd generation iPod Shuffle. The 2nd had real problems updating the "Last Played," "Last Skipped," and other settings in iTunes so I wasn't that sorry to see it go belly up recently.
But the 3rd Generation's problems in this regard are so much more complex. I want to use Autofill but right now it updates the wrong songs on the Shuffle (as viewed through iTunes) which is fine, I guess, because the main music library doesn't get updated at all.
What is going on? Why is it so difficult to play a song on a Shuffle (whatever the generation) and have these settings update correctly in both the Shuffle and iTunes?

I think it is a virus on your shuffle or it is on another file extension. If it is a virus try to reformat it.

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    QuickTime Feedback
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