Outlines are not displayed when printing. If you want a printable table of contents, you have to create it by hand, and merge it into the PDF produced by calibre. I suppose I could add a feature to the PDF output to generate a printable ToC, but, that's a fair but of work and if I do that, then people will want ways to customize the appearance of the ToC and I dont want to open that can of worms.
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