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Originally Posted by inkyichi
From what you stated above if i backup from my older copy, then use the option in the books content menu, to copy the rest of the books, then I will have to manually go in and add the series info and the ISBN information for the rest? Is there a way to then take the series information and make collections in your kindle?
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When you add a book to the library from your device, Calibre will read whatever metadata is stored within the book. I don't know which fields can be stored in a MOBI, but you should get most, if not all, of your metadata that way.
As for creating collections on the Kindle, I believe there's a plugin out there called something like the Kindle collection manager.
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Is there a program that will auto back up your library to a different location as you add books?
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I don't know, I backup manually. Other members may be able to help you more, I remember reading discussions about backing up a few times.