This turned out to be a different problem entirely. I called Microsoft and we eventually tracked it down.
At one point, I attmpted to set up RRAS on this particular box. During the setup, it asked me if I wanted to set up static packet filters. I hit yes, without really thinking. That broke internet access on my machine for several hours. Then - I went into RRAS to fix it. In the RRAS console, I went to IPv4- > General. Right click on the NIC and click on inbound and outbound filters and alter them from "drop all packets . . . " to "receive all packets"
But what I didn't notice was that it says "receive all packets EXCEPT THOSE THAT MEET THE CRITERIA BELOW"
In the list of criteria below was port 443 on 172.16.1.5 - the IP address of my machine.
What we were able to see was that I could not telnet to port 443 on 172.16.1.5. But I COULD if I did a telnet to 127.0.0.1 on 443.
Anyway - this was the cause of what broke my server - it wasn't transmitting any traffic on port 443 because of this.