Fixed it. (lol)
As soon as I posted this I figured out the problem. (murphy's law) I figure I'll leave it up for anyone who might run into a similar one.
We are behind a Coyotepoint Systems load balancer and that means every webserver in the network has a private IP. When you dig to the same box in the private network that you're digging from it's basically sending what is called a double NAT.
This means it's asking for the public IP but the load balancer is saying it's the same thing and so it's hanging.
Anyhow, to correct this is simple: Just add the
www.yoursite.com to /etc/hosts for the private IP and prefix.