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Does calibre start if the device is not plugged in? What OS are you running?
The first thing to do is start calibre in debug mode. You do that by running 'calibre-debug -g' (no quotes) from a command line.
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Sigh. OK, this one's my fault. I moved Calibre & the library from my flash drive to my network at home. Everything worked great at first UNTIL I rebooted my machine. The drive letter mapped to the Library share was "Disconnected" and Calibre wouldn't start. Simply clicking on the drive in Explorer reconnected it, which allowed Calibre to run.
Any chance there could be a check to make sure the library is available when starting Calibre?