Artwork in iTunes won't transfer to iPod

I'm having a little problem with my iPod Nano 4th Gen. I'm running iTunes on Windows XP. Everytime I create a playlist in iTunes and transfer it to my iPod, half the artwork is missing in the iPod playlist. All of the artwork is there in iTunes. I really don't want to have to add these all back in manually.
Can anyone help?
Cheers, Kirsten

Hello firelight789,
I would try restoring the Nano to factory settings via iTunes. This will clear your iPod's artwork cache and rebuild it. Here are instructions on how to restore your Nano.
http://support.apple.com/kb/ht1339
B-rock

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