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Calibre won't sync automatically with your Kindle. You have to load the books from Calibre to the Kindle manually, but you can do it in batches, not one by one.
A warning: Kindles take a long time to index after new books are loaded, so it's best not to dump your whole library on your Kindle all at once. Also keep your Kindle connected to a wall charger after loading the books, otherwise the indexing will be extremely slow. You can check the indexing by searching for a nonsense string of characters, if there are books still unindexed, the search results will display them.
Generally the process of sideloading via Calibre is pretty smooth and at least I have encountered very few bugs.
Last edited by Sirtel; 01-04-2020 at 05:41 PM.
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