Protected Content Membership Levels work for one user but not another

My question is not about WPMU DEV Dashboard but it was the only available selection in the dropdown above. I have Protected Content installed on this site and am running into a weird issue. The client created a test user and assigned the user to a specific membership level but he can't see content that the should be able to see when logged in as that user. I created a completely different test user and assigned them to that same membership level and I can see the content when logged in as that user.

Why in the world is this happening? How can we fix this?