trying to create accessibility tag doesn't create a tag in Acrobat, then the pdf breaks

Sometimes when I am trying to create a tag, Acrobat won't create a tag. It just doesn't do anything. Then my document tags won't be able to be found any more by searching for them, like it's broken the pdf. Like it's a bug. It seems mostly to happen when I am tagging a figure, but sometimes it is text. If I don't either Quit and not Save, or Revert, my whole pdf will be ruined and I will have to start from scratch. And it will happen over and over while I try various fixes to try and get the bit of information tagged. I do all kinds of things, digging into the Contents window, etc., to get the troublesome bit to tag. Finally one of my methods will work. Wondering if anyone has had this happen and know any tricks on how to tag these broken bits, or avoid them in the first place. Native files are usually Word docs. Also, how to rescue a pdf that has broken (tags become unfindable) if I don't realize it's broken right away.