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I believe that the Kindle Fire is a MTP device1 MTP devices are not supported by MacOS so you cannot connect to your device via USB which would explain your problem.
I believe that a common solution is to use an app like Calibre Companion at the Kindle end, and then make a wireless connection to that app. Calibre Companion can then pass the books into the Kindle eReader app. This provides good integration with calibre.
An alternative is to send books from Calibre via email, and let the Kindle sync them down from Amazon.
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