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My iPod classic that I haven't used for a few years only syncs around 3,800 tracks out of around 4,100 that I have as part of my library, even though the "entire library" box is checked on the device in itunes.
iPod classic
Hi there,
You may find the artilce below helpful.
Some songs in iTunes won't copy to iPod
http://support.apple.com/kb/TS1420
-Griff W.
iPod classic syncing issue
