I was having a similar problem helping a friend to set up email to kindle using gmail. Books seemed to be sending ok but were not arriving. At the same time I was able to send and receive using my own previously set up system, so we knew it wasn't a server issue. Eventually turned out that Calibre needed him to enter his @googlemail.com email address (rather than gmail) it's a very old address and don't think he has ever clicked the link to convert to gmail. Anyhow also remembered to add the googlemail address to settings in kindle approved emails page, and now working fine. I hope this helps someone - we spent hours trying to figure out why it wouldn't work.
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