If you are pulling books from overdrive, you can pull the covers from there too.
Go to the overdrive page for the book in your web browser, right click on the image, (e)dit the book metadata in calibre, right click on the cover and paste...
I've noticed that sometimes the book has a good cover internally, sometimes the one in overdrive is better. I don't know if the kindle driver supports sending covers from calibre, but the kobo driver does.
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