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I assume WINDOWS? (please always tell us what OS and version when asking about file issues).
Windows (and others) Must see the device (in explorer...) before Calibre has a chance.
Fix that. Common problems:
Anti Virus / security blocking.
Using a 'charge' (only) usb cord (these don't have data wires, only 5V), bad/disabled USB port (use device manager to see if any USB has issues)
Bad device (port) that still allows charging.
Note: (some?)recent Android come up in Charge only. You must THEN, enable File Transfer mode... This is not sticky and must be done every connection (USB options on the device)
Linux only supports 1 USB MTP device at a time,
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