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I have successfully converted all my calibre tags to Kindle on-board collections. It worked well, because my tags were always the same as the Kindle collection I planned to assign them to.
My question is, whenever I now tag a book in Calibre, will it automatically send it to the matching collection when I place that book on the Kindle? First time, I don't think it did this. I did not manually assign the collection on Kindle because I was aware that Calibre will overwrite Kindle tags; I just quickly converted ALL tags to Kindle collections again. It's not too much of a hassle, but I'm assuming that is unnecessary--that the collections will be assigned automatically in Calibre as long as the tags mirror them. Right? Hope I'm being clear.
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