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How many man hours have we all spent wrestling with this Calibre to Kindle email problem? I think I have tried every solution suggested. Calibre says the email was sent successfully. Amazon says there was no attachment. The only solution that works for me is to completely disconnect from Calibre and to use Outlook with my normal email client, attach the appropriate MOBI file and send it to My Kindle. Bang, first time every time.
Highlighting the book in Calibre, following the path to the file, right clicking and sending that way did not work for me. I suspect that if Amazon sniffs Calibre in the transfer a switch is flicked.
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