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QUESTION: Do I just highlight the book I want to re-convert in Calibre and hit convert? I guess what i am asking is will the conversion process just override the last mobi version in Calibre or do I need add the book again (in mobi) and then re-convert.
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Just highlight and convert (mobi -> mobi) no need to delete and re-import. It will overwrite the mobi that is currently in your Calibre library.
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Finally, once I have re-converted the book, should I add it again to my Kindle and the iPhone simultaneously since this is a new version of the book?
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Yes, it should be the same file loaded on any of the devices you wish to read the ebook on.