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Dude, malamang you itunes mo di compatible sa ipod firmware mo. Try to download the lates itunes kung di gumana hanap ka ng lumang version ng itunes. Pag na-read na yung ipod mo, DL mo yung latest upgrade for both itunes and ipod firmware.
+1. Either that or you have a bad USB port. Minsan may message na lalabas na message na kelangan mo i reformat iPod mo pero it's usually just the port. Ano ba iPod mo and iTunes version?
ung ipod nano... na 1 gig lang... tas itunes 7...