I wish troubleshooting all Microsoft products was this easy. Download the SSL Diagnostics Tool from Microsoft.com, install and you get a nice GUI that runs a test against each website you have setup in IIS, letting you know if any sites have problems. In my case, it found that I had deleted the sspifilt ISAPI filter, which unbeknownst to me, provides SSL functionality for IIS.
Hey Aaron~
I am glad that SSL Diagnostics helped fix your problem.
The design team, comprised of myself and others at Microsoft, set out to help those who are new or veterans of IIS (and SSL) and this is good to see.
If you have questions in the future, let us know – ssldiag@microsoft.com.
~Chris