Whew. Finally after some trials and tribulations I have managed to get rpc over http(s) working with my home exchange server. I followed many of the guides online and there are even some tools to help aid the process of the configuration. Exchange 2003 with service pack 2 and the aforementioned guide/tools makes the setup a breeze.
I still couldn’t get outlook to connect to exchange outside my LAN. What good does that do me? Not much which is the whole reason I wanted to get exchange running over http. Outlook would fire up and eventually prompt me for a login (good.) However it would never fully connect. The problem: SSL certificates. I haven’t paid for an SSL cert yet so I use my own certificate authority to grant the certificate. Ok, all set. Nope. I had to make sure the certificate had the FQDN of the exchange server in it and also import that certificate into my trusted authorities in IE. Presto! Now we have connectivity.
Daniel Petri advises that most if not all of the connectivity issues are related to certificate issues. Make sure you check your certs and if possible, buy one from an online vendor so you don’t have to import anything.