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Try putting on a mains charger for 24 hours. Don't use it during that time.
This is my standard treatment for a sick ereader.
Afterwards, try doing another restart.
If that doesn't work, attach it to your computer via usb. If you can see the kindle as a drive, try directly adding a book to the 'document' folder.
Eject the kindle using whatever is standard on a Mac, but not via Calibre. Leave the USB attached to the computer for an hour or so.
In the meantime you should be able to see books on the Kindle.
If this basic stuff doesn't work - hope that a techie comes along to this thread.
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