1. there is no " of course" about it
the forum is full of issues where windows fails to see a device at the other end of a conencted cable. mostly Kobo, but can happen with Amazon tablets also.
2. so you have a fire tablet, not a kinlde. that is progress.
if you now narrow it down to problem with connecting to content server vs problem with connecting as a wireless deivce vs problems with both options, that will help others to help you
when you connect to content server it is not calibre that does the "seeing". it is the app on the device that tries to "see" a server. assuming you have already checked that you have given correct info on the app preferences screen, then there is a log on the device what you can access and send to the developer...
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