Bookmark issue

I have a couple of strange bookmark issues within my word doc… The first one is that I have bookmarked a section, one part of that section is a handtyped heading on the word doc the other is text that passed if selected next to the heading, for some reason the bookmark works fine for passed through txt but no for the heading any ideas?
The other issue is that we have bookmarked several pages towards the end of the document, most of these bookmarks work fine except the last one which leaves us with a blank page.
The two sections are:-
Bespoke Condition on page 19

Thanks for your request. Could you please attach your document for testing and provide me the code that will allow me to reproduce these issues. I will try to reproduce these problems and try to help you.
Best regards.