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One thing you can check quickly is to see if you have any other iDevices plugged into your computer. If you do, then Calibre will not see either of them. There can only be one iDevice plugged in at a time.
I sometimes have my iphone plugged in to the computer to charge and forget it's there when trying to put books on my iPad. Never works, and always takes me a few minutes to realize I have them both plugged in.
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