An interesting tool can be found in the IIS Resource Kit that proves its worth time and again... Selfssl.exe is an unsupported tool that can create a self-signed certificate for use on your website. While not a replacement for a registered SSL Provider (have you seen Startcom.com?) this little tool can help test any website that requires Secure Socket. I also have been able to use this for LDAP/S when testing my ADAM server configuration.

The key to this tool is it's ability to complete the self generated certificate step even if IIS isn't running on your server. Sure you get an error indicating Selfssl can't talk to the IIS metabase, but by then the certificate has been created and saved into your store... So download it from Microsoft and give it a try and see if it works for you...