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My iTtunes/iPhone syncing works perfectly except for this odd behavior. One song syncs every time. I never listen to it really, and I've loaded other albums/songs from time to time with the expected behavior, but regardless the same song gets uploaded every time.


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Do you have it in a playlist that gets synced? Also, things may be different if you have manually manage music on. Any more details on your settings?

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I don't manually manage music, and it's not in any play list. Even if it was, shouldn't it get synced once and never again? Wouldn't the entire playlist get updated if need be? This song is synced every time... I hardly ever change anything in my library these days. 99% of the time, nothing in the music library should need syncing. – robot Oct 6 '09 at 23:46
You might try turning on manual mode, deleting all music, then turn on regular sync back on to the settings you had and letting it resync all media. If I remember right, I had something like this once and doing that solved whatever hickup there was. – Troggy Oct 7 '09 at 14:34

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