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I guess I am lucky also because it works every time for my K2I, the only time I have problems is if the book on the kindle is not where Calibre thinks it should be. To correct this I just send a second copy to the kindle, rename the mbp to the same as the second book, delete the first one and then re-run the annotations download. I run into this problem because I use a specific template for the naming conventions of my book and if the book was put on the kindle before I changed the metadata in Calibre, I could end up with conflicts.
Nyn
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