iPod.iTunes v4.9.32
iPod song, video & playlist sync in 2 directions.
iPod.iTunes Editor's review
iPod.iTunes for Mac helps you detect and transfer missing songs, videos, podcasts, or playlists from your iPod to your Mac or the other way around, without deleting existing files on the target device/computer or creating duplicates. It comes with a convenient wizard that makes file transfer easy and a couple of other nice features. If you want file transfer capabilities that iTunes doesn't offer, this app is for you.
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