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Kindle, Calibre and lost place in book

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Hope this is in the correct place. If not, hopefully a mod will move it for me.

General info:
  • Calibre 1.9.0
  • Alf's tools: v6.0.8
  • 3rd generation Kindle
  • Kindle Paperwhite
  • Kindle DX
  • Mac OS 10.8.5
  • All software on the 3 Kindles is up to date

I've used Calibre ever since I got my first Kindle and I've never had a problem. However, since version 1.x, I have an issue with any and all books losing their place, bookmarks disappearing, and highlights also disappearing. This always occurs if I move from book to book, and will occur once in a while if I keep reading the same book.

I've completely wiped and restored all of my Kindles, and if I then download all books either directly from Amazon, or transfer vis USB directly from Amazon, everything is fine.

As long as I don't use Calibre, everything is fine. Once a book is taken into Calibre the problems start. I've both transferred via Calibre while in the program; and also downloaded books to my iMac, converted in Calibre, and then instead of using Calibre to transfer the book, I physically located it on my hard drive and drug it over to the "Documents" folder on my Kindle. The problems crop back up. Worse, any book already directly downloaded from Amazon also starts behaving in the same fashion.

I'm frustrated and hoping there is an answer to this.

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