Some songs do not copy from iTunes to iPod

This is very frustrating. I have a 5th Generation 60gig iPod. There are about 20,300 songs in my library, none of them from the iTunes store. All legal, all owned by me and I have the CDs to prove it. When I update the iPod all but about 4 or 5 songs copy over. The frustrating thing is there's no way to find out which songs are not copying over to the iPod, so I can't tell if there's a problem with them or what. AppleCare tells me the only way to find out is to visually compare the list on the iPod with the list in iTunes. I have 20,000 songs here and allegedly one of the most powerful computers you can get and I have to compare two nearly identical lists visually?? Oh, by the way I'm running 10.4.6 and the latest version of iTunes and the latest iPod update. This never happened with my 4th Generation iPod. Any thoughts at all of what to do would certainly be appreciated.
Powerbook G4, iMac G5   Mac OS X (10.4.6)  

Are you basing the few that don't get sent to your ipod on the file count? Could there be duplicates? I've noticed that there are some of my movies that don't get sent over but I usually get a warning that they aren't in a compatable format.
There is an option in either file or edit (can't remember exactly where, I'm at work) but you can filter to show all the duplicates. I've noticed that when I drag files over to be copied to my ipod and there are duplicates, it only does one.
After you find the culprits, another thing would be to export the file to your desktop. Delete it from iTunes then reimport it making sure of the file format.
just a thought

Similar Messages

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    http://support.apple.com/kb/TS1408
    iTunes 11 for Windows: Symbols used in iTunes
    http://support.apple.com/kb/PH12306
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    Are you basing the few that don't get sent to your ipod on the file count? Could there be duplicates? I've noticed that there are some of my movies that don't get sent over but I usually get a warning that they aren't in a compatable format.
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