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Didn't Amazon change the way Kindles mount into the file system of a computer a version or two back?
I found a utility for the Mac from Google called Android File Transfer and use it to connect to the Kindle and send files to it. That has worked for me.
For this most recent update, I used one of my PC laptops and had no issues.
I just checked again on my MacBook Air and the Kindle Scribe no longer mounts in Finder. I'm quite sure that it no longer appears to the OS as though it is a USB drive. Now it uses a proprietary format that Windows has built into the OS, but Apple has not. So, give the Android File Transfer app a go and you should be okay.
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