iTunes allows downloading TO the ipod only, not the other way around. There are shareware programs that take care of the reverse transfer like iPodRip (mac), it likely results in loosing the ID-tags of the songs, though.
my ipod nano 1st generation wont hold my songs once i disconnect it . itunes detects the ipod and i...
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my ipod nano 1st generation wont hold my songs once i disconnect it . itunes detects the ipod and i can drag songs into the file. however now it wont hold the songs on it. they wont save to the actual ipod