It would have been helpful if you gave the full scope of the project at the outset. What you're now asking for would require a complete re-write.

Re:
Highlighting numbered headings can be done by changing their Style definitions (you are using Styles, aren't you?).

Re:
To see what's involved for these two aspects, go to: https://www.msofficeforums.com/word/...sage-same.html. Although the code there does somewhat more than you're asking for in this case, it is similarly complex, as the code has to both build the list and generate the output.

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Cheers,
Paul Edstein
[Fmr MS MVP - Word]