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Do you have the same problem with just dragging and dropping books without calibre whatsoever? IF you still do then it is not a calibre problem, might be a book that is corrupted or something.
For your info, even if the files are physically there on the device but are not accessible from the reader, it is because they were not added to the reader database, That is what processing content is supposed to do. So if 1 file has something funny maybe it's hanging on it.
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