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Member Since: Nov 26, 2010
Posts: 114
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Manually managing Music and Videos, you can just click on the file you want and drag it to your iPhone. You don't have to use the tab at the top.
You see a song in the list: "Yesterday by the Beatles" Normally, you'd double click it to play it. Instead, click and hold, then drag it to the left where you see your iPhone in the list. It will then transfer to your phone.

To get something that you downloaded over the air off your iPhone back into iTunes, on the left where your iPhone appears in iTunes, make sure the little triangle next to iPhone is pointing down and you can see the sub folders (Music, Movies, Playlists Purchased, etc) look for Purchased CMD+click and pick transfer purchases.

Maybe I understood your questions?
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