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Late last year I decided to sideload via Calibre some sets of books to my Voyage, I loaded each set one at a time, then loaded that set into a collection. I honestly can't remember if i got the messages or not (I had a workaround by then I'd adding a page of titles at a time,therefore getting only 1 pop-up per page) but I vaguely recall being surprised by NOT getting the message.
It may be that if the books are loaded via USB the message is suppressed but I no longer do that with my Kindle, all my kindle books are cloud based, even personal documents.
If I wanted an ereader that I always had to sideload books to via usb I'd not have a kindle I'd only have a kobo. I think kindles are best used when looking at the whole package of how an ereader works.
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