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Converting through Calibre arises when you already have a lot of books in the .epub format or another format not readable by Kindle.
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I have a few PDF's (fiction not technical) along with epub files and RTF files, last night I simply highlighted every file in my Calibre Library and clicked convert, as it was a multiple task (767 files in one go) Calibre just asked me to select the outward file, I selected MOBI and Calibre took about 2 hours to convert the lot. It seems to have done it seemlessly.
I obviously can't test loading them onto a Kindle until mine arrives, but Calibre certainly seems to have done its thing. The whole process was quicker and simpler than I anticipated.