Hello Dan,

Once you enable SSL for a website in WebMatrix, it defaults to port 44300 and does all the bindings in the background. I am hoping that you tried to change this port to 443 in the config file. Once that is done and saved, you also need to modify the binding in http.sys. You would need to delete the existing entry for port 44300 and add the entry for port 443.

To do this, you could use httpcfg (WinXp/Win2003) or 'netsh http' (WinVista/Win2K8/Win7).

Here are the commands for netsh:
1) Get the appid and certhash for the existing entry of 44300 (I assume, you are going to use the same certificate which WebMatrix installs by default. If you want to change the certificate as well, get the certificate hash of the certificate from the certificate store): netsh http show sslcert. In the output search for entry for port 44300 and copy certhash and appID.
2) Delete the entry for 44300: netsh http delete sslcert ipport=0.0.0.0:44300
3) Add a new entry for port 443 with certhash and appID copied in step 1. netsh http add sslcert ipport=0.0.0.0:443 certhash=<certhash> appid=<appid>

After configuring the entry in http.sys, you need to restart http service for the changes to take effect.

net stop http
net start http

Let me know if you have any question on the steps.

Divya