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I too am just a beginner and unfortunately having the same problem,
I have a kindle white when I use the cord to transfer from calibre to device it will transfer one ebook but when I try to send another book it will delete the first book that I had successfully sent to the kindle.
In addition I was able to email a list of ebooks to my kindle but now I cannot email any books from calibre to my kindle but I can email purchased books from amazon to my kindle.
Please help
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