After doing some fairly inconsequential set up of a new Windows 2008 server instance it will cease responding to any connection attempts after a reboot. RDP, HTTP, HTTPS, you name it. I am unsure if this is because the installation has become corrupt or if something in Windows 2008 is triggering security measures and simply blocking all inbound connections.
A user on the Amazon forum's led me to a solution. The problem will occur after binding an SSL cert to a website in IIS that was not issued from a recognized CA. I'm not sure if this would be classified as a bug or by design but it's confusing either way. To resolve the issue you must verify the existence of the issuing CA's certificate in the Trusted Root Certificate Authorities store. You can do this with the following steps:
If the issuing CA of your SSL cert does not exist you must import it into the store. You can do this by retrieving a
cer
file for the issuing CA, and importing it by right clicking and selectingAll Tasks->Import...
and following the steps in the wizard.