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An issue in the past was that books loaded into Kindles through Calibre appeared as 'personal documents' rather than as a 'book' in the Kindle, upsetting causing the reading state sync to not work if you were reading the same book for example through the Kindle app in your smartphone also, very annoying, and goes against the promise of ebooks. I hope they have a fix for this.

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I've gone through the motions of emailing the book to my Kindle, which allows it to be downloadable on other Kindle devices or the app, and also syncs up reading location.

Doesn't work for huge books, but has been a great boon for most books!

Right, that's actually my standard Calibre use case: Load book into Calibre. Convert it to MOBI if needed. E-mail it to my Kindle address.

It then pops up everywhere I have a Kindle app, mostly my iPad and Galaxy S9.

Huh. Now that I'm thinking about it, it seems like this would be even easier to do from the command line...

If you fill out the "Sharing books by email" in Calibre's settings, you can just right-click a book -> "Connect/share", "Email to example@kindle.com". It'll do the conversion for you (if necessary).

I'd advise a separate email address for this functionality.

That must be a very long time ago. It worked fine with my Kindle 3 which was released in 2010

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