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Originally Posted by dwig
If a sideloaded book has what the Kindle thinks is an ASIN number it will sync. If a downloaded book doesn't (e.g. books from sites other than Amazon, ...) it won't.
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Further clarification... notes, highlights and bookmarks don't sync on non-Amazon content. Period. "Furthest read page" WILL sync on non-Amazon content with a little diddling. But In addition to the ASIN number, the CDEType needs to be set to 'EBOK' for ANY type of syncing to occur. Personal documents (CDETYPE 'PDOC') will not sync at all - even if you give it an ASIN number.