Territories Just Don't Work

Territories Just Don't Work

I have been on chat and screenshare support for the past 3 days and am getting no resolution so hopefully, someone here can help me.

I am the Super Admin of my organization. We publish books globally. I want to break down the books into territories so users can only see the deals from the territories they are working in. 

What the problem is:

  1. I set territory rules and run them but the deals are not updated to the territory. When I do the search I find 100 deals that should be converted by the territory rule but after running the rule - no territories are assigned. Here is a Youtube Video Showing the exact problem: https://youtu.be/uSnP8CQXWh8
  2. If I go into a deal and manually assign a territory it shows on my (Super Admin) profile that the deal is in that territory. But, when I log in as a test user that is not part of the territory at all, I can still see the deal in my dashboard and make changes to it. However, when I go into the deal, it shows no territory assigned. So when I log in as Admin, the territory is assigned but when I log in as a test user, the deal has no territory assigned. Link to Video explaining the problem: https://youtu.be/rw757CxQiUY
Please Help