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I mentioned this issue in another thread, i.e. I had been using my old original kindle as the device when I downloaded to my mac. Basically, they now have compatible devices and the older devices don't support the new AZW3 format. I suspect the question of downloading an ebook depends on if it's been updated to the new format or not, i.e. the publisher has updated the book for some reason or another. I generally get 2 or 3 book updated notices a week.
My solution was to buy a new Kindle. While I normally read on my iPad, having a light, long battery book is useful in some situations such as backpacking. All my ebooks are format shifted to epub so I can read them on my iPad.
There are a lot of reasons to remove DRM and keep backup copies. Ebook stores going out of business, changing devices, etc...
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