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Originally Posted by sadievan
1. Does it just overwrite the current file or does it make another mobi file?
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If a given output format already exists, Calibre overwrites the file. There can only be one entry per format per book.
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2. Is it ok to do a lot at once. Or should I convert in steps, so many files at a time. I have approx. 135 books in Calibre right now.
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Calibre queues the conversions and works on them according to how many CPU Cores you've given it.