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When you plug your reader into your Chromebook 's USB it should ask if you want to 'continue reading' or 'manage my library'. If it does not do that, it would seem to me that your Kobo reader does not get the 5V power from the Chromebook through the USB cable. Did you try attaching a portable disk drive or any other USB device (USB mouse for example) and see if that works? Do you have multiple USB ports and tried them all? This problem is not related to Calibre for sure.
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