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Amazon does not generate page numbers for Personal Documents, as far ask I can tell (none of the formats it accepts for conversion have any way to specify page numbers, except for PDF, and you don't want to go there).
Calibre generates them for you if you side-load the file, but personally I'd rather be without calibre page numbers since they do not relate to page numbers of any print edition, and I don't find 'unreal' page numbers of value. YMMV.
You might be able to import the file to calibre (over USB) after downloading from Amazon, then have calibre 'copy to device', which should get calibre to create an .apnx file with its pseudo page numbers in it, which nevertheless should still sync and backup highlights to your Kindle account etc. Kinda roundabout, might not work, but maybe worth a try.
Or write a plugin for calibre to add apnx files to everything on your kindle that does not already have one...
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