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Originally Posted by eschwartz
As jhowell said, the Send-to-Kindle service modifies all books to set the cdetype to PDOC (and set the exth 113 to a Personal Documents Service-format ASIN).
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Bummer, but thanks for the clarity.
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Since this happens after you send it once the book reaches Amazon's servers, there is no workaround unless you want to hack Amazon's servers and "fix" their service for them. 
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Let's leave that option for later.
While I'm at it, though -- a further question about Whispersync and PDOCs: if a PDOC is sent through free.kindle.com (or if I set my WhisperSync budget to 0), does Furthest Page Read still sync through 3G?