Setting up SSL on IIS and OWA
I finally went through the steps of setting up SSL on my email server. I never really did find an article talking about what exactly I needed. But since I had already setup Certificate Server to be my own X509 certificate authority to use with S/MIME SMIME. I decided to jump in from there and see what happens.
Since my domain already had a registered Certificate Authority, when I went into IIS and my web sites properties. I found that I could create a 'new' certificate, and fill out all the fields I wanted. I made sure the name of the certificate was the FQDN of the web site I wanted. It then automatically presented my CA that I had installed a week ago, and click... it was installed. Very clean. Definately easier then following up with Instant SSL. Then from a client perspective I still get a popup stating my site isn't signed by a root authority, but after I install the certificate, it works as cleanly as a site that uses a InstantSSL or Verisign Certificate.
Along the way I found the following links useful, but not helpful in solving my specific problem.
HOW TO: Set Up an HTTPS Service in IIS
Setting up SSL with a SelfSSL certificate on Windows Server 2003 - FREE SSL without Certificate Server
How to redirect to a secure exchange virtual directory and enable Forms-based authentication