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I just received my first Kindle today after using a Sony for 10 years. I was having trouble with this exact issue. I was able to transfer the books to my kindle, no problem, but there were no covers. I like covers so I can see the pictures (just my preference).
I tested inserting the book into Calibre (as I hadn't read all the comments on other suggestions), selected the publishing date to be undefined under "Edit Megadata individually". Then I transferred the book to the device "Send to device." It worked for me and I was able to get all my books over to the device with a cover. Thank you. I am sure other ways work, but since this method worked for me I didn't need to read further.
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