Parent Category Not Showing With Listings in Sub Category

I know that GD will not show empty categories.

I am having issues with a parent category not appearing, even if there are listings in it’s child category. Is GD intended to work this way?

What I attempted to do was add an existing listing to an empty parent category as well as the child category it was already in so it would show the parent category. I noticed that when I do this the parent category not only shows up but the listing count includes the listings in the parent category and the child categories. So I am thinking this could be some sort of bug?

Investigating further I went to a category that was showing “O” in the WP Dashboard Places>Categories under “Count” – I right clicked “View” to “Open Link in a New Tab” and there I see the category is in fact public, with listings from it’s child categories.

You can replicate this by looking for “Weddings in NH” in the category list here:
https://nhtourguide.com/wp – You will notice the category is missing.

Then go here: https://nhtourguide.com/wp/places/category/weddings-in-nh/

Maybe it has something to do with the fact I used the GD PHPMyDirectory Converter?