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What version of iTunes are you running? If you don't have the latest version of iTunes, there might be a bit of a problem with it. Maybe you should try using different version of iTunes, I know that a few of my friends were having trouble with iTunes 9, so they just upgraded and everything works fine. If all else fails, you can SSH into your phone, save whatever data you want to save (jailbroken or not) and restore your iPhone.
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