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I recently bought a PW, and had the same issue.
.mobi files transfered by USB to the PW (using simple drag&drop in an explorer) did not have the cover shown on the PW.
You could use Calibre for USB-transfering-to-device.
As far as I know, the PW depends on a specially named thumbnail jpg file, in a special folder. That thumbnail gets created automatically if you buy/download from Amazon.
Calibre (after a certain version), figured out the need for this thumbnail, and creates it (there's also a pixel size restriction for the thumbnail)
Alternatively, you could send the book with "email to Kindle Amazon Cloud" ...
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