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This may not apply to you, but it is what screwed me up for a while before I figured it out (i.e., read about it here). Make sure your iPad is the only iDevice plugged in to your computer. I'd have my iPhone plugged in just to charge it and then when I tried to connect calibre to my iPad it would not work. Once I unplugged my iPhone, it worked fine. I do occasionally need to restart either calibre or the calibre connection within Marvin on the iPad to get them to hook up, though.
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