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Snart, there is a known issue Amazon server end where if you convert and de-DRM the ebooks in Calibre that the cover images won't show, I'm thinking this is the same problem you have.
The way to fix that is to go into the SETTINGS and OUTPUT OPTIONS and then go down to the version you're exporting / converting to it might be Amazon AZW3 or MOBI, then there's a tick box for "Enable sharing of book content via Facebook, etc WARNING: Disables last read syncing". This is the part where it will add the cover image back into the book, but it only happens when you go to convert the book again. You can then right click on the book in Calibre and convert it, take the output file wherever it saves it and then transfer onto your Kindle.
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