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I'm currently typing up notes in Microsoft Word using the outline mode but when I try to print this document it loses the outlining format and reverts to the original document

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Outlining format by design will not print exactly what is shown in outline mode. If you want your document to look like what's on the screen when you print it, design it in print layout view (View tab -> Document Views -> Print Layout).

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You could put in a table of contents, tied to the headings you have used, then just print the pages which have the TOC on them

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