floepie said:
Good god. Found the answer. It must be bug. Found it here:

Pinning folder links to Jump Lists in Win7 - Topic Powered by Eve For Enterprise

In short, you MUST have "Store and display recently opened programs in the Start menu" checked in the Start Menu properties privacy section. Well, that certainly saved me a lot of time...
Glad you found the answer. I noticed that a build or two ago.

It makes sense that you don't see recent programs show automatically unless that's checked.

It doesn't make sense that you can't pin things yourself unless that's checked.