CC is the COMPANION to Calibre on your PC. It does not DETECT devices because it runs on the DEVICE and it expects that device to provide a viewer.
You have a few, non-elegant, options
1) Use your phone w/CC or just a browser to find books in your Library to read.
Then get a USB 'transfer' cable to connect your phone to your reader.
Then use your phones file manger to copy the file to your reader.
2)use the (store) browser on your reader to connect to the 'Calibre Content server' running on your PC.
NOTE, no 'on the fly' conversion is possible with this process. The format must already exist.
Very few dedicated readers support Blutooth (allows file transfers) which would be the alternate to the USB cable in #1
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