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hey, so this happened to me too. I don't know what caused it, but the .metadata.calibre file on my kindle lost the uuids for all of my books. i fixed this by looking up the uuids in my calibre library's sqlite database (metadata.db) and restoring them to the entries in the .metadata.calibre file before connecting to calibre again. because the filenames on my kindle included the calibre library book id, looking up the entries was straightforward. i'm not sure that this is the default, though
if you don't want to go through this, you can move/delete the .metadata.calibre file on your kindle, connect to calibre, and resubmit all of your books
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