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Can't sync entire iTunes library ?

Hi folks,

iMac

iTunes

iPod Classic 160 GB

I want to move my entire 130 GB 12,100+ song iTunes music library onto my iPod Classic.

I've re-set the iPod Classic to its factory settings and have @ 150 GB free.

The problem I am having is that when i plug in the iPod Classic and say "Synch" - it only thinks that it has to sync the 400 or so songs that exist in my recently Purchased Playlist - it isn't attempting to move all the songs in the entire library.

Any constructive / helpful ideas would be most appreciated.

Thanks,