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I have run across a number of pdfs that Calibre would not convert, even though they were searchable, that is, contained some sort of text. Calibre uses pdftohtml to extract the text. In the case of the ones I've found, using pdftohtml from the CL failed, but using pedtotext worked. I guess Word can find some text Calibre can't.
A pdf can contain just about anything. As theducks said, it depends on how it was made.
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