I'm having the same issue (Calibre won't see my Kindle Paperwhite) HOWEVER OSX is seeing it, it shows up in Finder. I've removed my saved preferences (~/Library/Preferences/calibre) and started fresh but still have the problem.
MacOS: 10.15.5
Calibre: 4.20
Kindle Paperwhite 2: Kindle 5.12.2
Nothing shows up in the debug log referring to any devices (e.g. USB devices on system: does not appear in my debug log at all). I have gone and checked items in the troubleshooting sticky post.
Last edited by BrendenM; 07-08-2020 at 02:24 PM.
Reason: More information
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