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Isn't calibre running ON the Mac??
If you're trying to use calibre to send an ebook to the Kindle for Mac application like it's a device, I don't believe it will work that way.
I'd use the "Save to Disk" option to save a copy of the ebook in Kindle for Mac's library folder. Or in Preferences->Behavior, uncheck the boxes for MOBI/AZW, etc... so the default app for kindle files (K4Mac) will be used instead of the calibre viewer. Or use the "Open with" calibre plugin to configure different apps.
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