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It's the way you save update the file in Calibre. Once you edit the metadata, ie change the picture, you do need to make sure Calibre saves the changes. (It's not just the DR that has this problem)
What I do to makes sure is, edit the data in Calibre, save it close Calibre and re-open Calibre to make sure the new image is picked up, then, sync the book across to the reader.
This issue is discussed in the Calibre forum somewhere.
regards, Howard
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