IPod won't download playlists it once did

My IPod won't download several playlists that it once did. I get a message saying that I have old iPod software and that I should download the latest software. I've done this several times and it still won't download these playlists. My G4 15" powerbook has the latest updates for 10.3.9.
How may I fix this?

XXX

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IPod won't download playlists it once did

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