Automatically Update Document Styles glitch

I've got a template with a defined set of styles. If I double-click the template to create a new document, everything works as it should.

However, when I attach the style to an existing document and select "Automatically update document styles", the heading styles do not update properly - or so it appears. If I then save that document (with the "bad" styles) and re-open it, everything looks like it's supposed to. If it was just for me, this would be fine, but this template is intended to be used by everyone in our department (and eventually the whole company), so explaining to other people the "work around" is not a viable option.

Anyone have any idea what might be happening? Is there a way to fix it?

Originally Posted by macropod

How are your attaching "the style to an existing document"? Or are you attaching the document to your template? Regardless, the "Automatically update document styles" setting takes effect when a document is opened, not merely by attaching a template or by copying a Style to a document.

The template is being attached through the Templates and Add-ins dialog (Developer > Document Template), and selecting "Automatically update document styles".

We actually have a set of 5 different templates we use. They have 6-heading multilevel list styles defined (with slight variations between templates based on document types) and assorted macros (for lists, keyboard shortcuts, etc.). I've been using them for close to 10 years, this is how I've always done it, and it has always properly updated the styles. We publish documents received from other departments and this has always been the first step in starting that process. It's never been an issue until today.

I recently made some edits to some of the macros and paragraph styles, but didn't touch any of the heading styles. After noticing the issue today, I removed the updated templates and replaced them with the old templates (which I had archived), but now even the old templates are exhibiting the same behavior. I even went so far as to find a copy of one of the old templates on another other tech writer's PC (as I know for certain it hasn't been "updated" since it was created many years ago) and have the same issue.

I'm genuinely at a loss.