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When I have wanted to send a book e.g. to my daughter's kindle, I just did it from first principles. no faffing about with calibre, gmx...
Just addressed a regular email to her kindle account, located the mobi or whatever book by using "open path" in the calibre details window, and attached the file to the email then hit send.
Its been a while but that always worked when I wanted it to. She just whitelisted my regular email on her Amazon page for receiving stuff, no other components needed, so less places for it to fail.
Our only stumbling block was creating the correct flavor of mobi, to get it accepted
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