This problem was driving me nuts with my Kobo Aura, a MacBook Pro, and Calibre. I learned a couple of years ago that not all cables will work for data and I was using a Kobo cable (actually labeled Kobo) but the connection was always hit or miss. Sometimes a MacBook reboot or a Kobo reboot would work and sometimes not. Today nothing worked and in desperation I tried using an OTG cable I had for my Samsung phone and Calibre instantly connected with the Kobo. How long this will last I do not know but it is the only solution that has worked for me, at least for today.
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