I have the same problem between my Kindle 2 and my Kindle for PC and Kindle for my Droid. The PC and Droid will sync with each other fine. The Kindle will pick up where the PC and/or Droid left off, but neither the PC or the Droid phone can pick up where I left off on my Kindle 2. I usually update my Droid phone in the mornings manually before leaving for work. That way, my PC will sync with it so I can read my books during my break or lunch on my PC or phone.
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