Just tried again was was able to capture an error message when my computer attempted to connect to my Kobo. I had Calibre open. Finder said that my Disc was not ejected properly.
calibre, version 3.6.0
ERROR: Error: Error communicating with device
IOError: disk I/O error
Traceback (most recent call last):
File "site-packages/calibre/gui2/device.py", line 88, in run
File "site-packages/calibre/gui2/device.py", line 511, in _books
File "site-packages/calibre/devices/kobo/driver.py", line 1856, in books
File "src/cursor.c", line 236, in resetcursor
IOError: IOError: disk I/O error
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