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In macOS Catalina, it should mount in Finder and you can drag files over to files/Kindle. I’m not sure if it translates to some command line. Probably some AppleScript automation is possible for that.
You might ask in calibre forum how it connects and moves files over USB connection, supposedly it detects device and can copy stuff over to it, I’ve never used the feature, but I’m guessing it is equivalent of a command line thing. But they recommend calibre companion to do it wirelessly.
The other way is to use cloud storage for your files (ICloud, Dropbox whatever that you have on your Mac), and just open with the vendor’s app or Files (after connecting the cloud services (calibre companion integrates with Files)). To me this is ideal as you don’t need to connect the 2 devices physically.
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