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markdek is correct, but to be totally clear, here is what worked for me today after reading a gazillion threads and trying various methods:
1. make sure your devices have "Annotations Backup" enabled.
2. load the book into calibre.
3. convert to mobi. even if it is already mobi, convert it again.
4. use calibre to email the book to one of your devices. this will put it in your amazon cloud.
5. if you want the book on another device (kindle, iphone w/ kindle app, etc), simple pull it down from your amazon cloud.
By doing this, I can now "sync to furthest page read" across all my devices, works great.
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