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Hmm, this was more complicated than I expected. My books almost always arrive to my Kindle first. Then after a while I connect with Calibre and copy them to my library. After that I take the new books and download Metadata and book cover. If I understand you correctly I need to then match that data with what I have on the Kindle? Obviously I prefer the newly downloaded Metadata (it contains tags and descriptions). Are you trying to tell me I can move that new Metadata over to the books on the Kindle? Or do I have to delete them from the Kindle and then copy back from the library? Don't know how comfortable I am with that, considering how it reports back to Amazon on a regular basis.
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