When you say that I have set it up so that I can hit the external website externally, I am assuming that when users enter login.domain.com/site/login.aspx they can see the login page and enter their credentials. Assuming that we have only one website in IIS(Default Web Site) follow the following steps Open IIS Manager and go to the properties of the Default Web Site-->Home Directory select the radio button A redirection to a URL and enter /site/login.aspx and select a directory below URL entered.
Note: This would only work if you have a Virtual Directory named Site under Default Web Site and within it you have login.aspx
If that is not the case please give a dispriction or the path where that file(login.aspx) is located on the server.
Imran