@cooldavidt: There is no sign of a Kobo device in that log. Is the device visible on the MAC? It has to be mounted as a drive by the OS for calibre to be able to access it. There have been a few reports recently of changes in the OS that means these devices aren't being mounted. I don't know the details, but it has been discussed here and in the Kobo forum. Though it isn't a Kobo issue, it affects other devices as well.
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