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The page numbers on the contents page do not change to reflect the new position of the bookmark
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Try Ctrl A to select the doc and then press F9 key to update.
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I can't seem to be able to manually tag the headings in order to cross-reference them
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You shouldn't have to tag them. Word allows you to cross-reference any text that is formatted with one of the heading styles. You can modify the appearance of heading styles to suit your tastes, or you can create new styles based on existing heading styles, if you don't like the built-in ones.