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If you have an Apple device (iPhone, iPod, iPad) attached at the same time then it could be interfering with detection of the other devices as Calibre will only recognise one connected device at a time.
If you are not interested in using the Calibre direct interface between Calibre and an Apple device (you can still interface Calibre to iTunes) then you can disable the Apple Device driver in Calibre under Preferences->Plugins->Device Drivers.
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