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A not-so-obvious reason iPhone sync may fail iPhone
iPhone syncing is tied to the other kinds of synchronizations your Mac may undertake -- like .Mac syncing. If a conflict occurs with the .Mac sync, the "conflict resolver" window will appear, usually accompanied by an orange icon. If you've got your dock hidden, you might not notice that the resolver has activated, since the window doesn't appear in the foreground. As long as that window is open, however, your iPhone sync will appear to hang.

This happened to me this morning, when I plugged my iPhone in. An automatic .Mac sync during the night had found a conflict, and having not noticed it, did a full reset -- which also failed -- of the iPhone before realizing what had happened. Resolve the overall sync issue, or dismiss the resolver window, and iPhone sync will continue normally.
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A not-so-obvious reason iPhone sync may fail
Authored by: paulofierro on Mon, Nov 26 2007 at 1:28AM PST
The same thing happened to me when Spaces was activated. The iSync window appeared on another desktop but the active desktop never switched. There wasn't any visual cue in the dock either so it took me a while to figure out why syncing the phone was taking so long.

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