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Originally Posted by meanSpleen
Its the software. You can drag music onto your ipod, but the software will not be able to find it because it organizes everything on the ipod to a reference ipod-library database. Syncing just creates and updates the lookup database with any changes to the files being stored/removed
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So why not do that, using it as a hard drive, and when he gets home, drop onto his comp, then transfer it back with iTunes?