redirect rewirte option in http profile causing looping

I have to believe that what you're experiencing is an application specific behavior. The Redirect Rewrite option will catch a redirect from the server and rewrite http:// to https:// in the Location header. But if what you're sending back to the server from the redirect is still not what the application is requiring, then it may attempt to redirect you again, and again, and again... It's difficult to say what that may be though. I've seen applications like SharePoint that only care about the Host header, and apps like Webmin that apparently care about the Host and Referer headers. I would start by examining what the application does in the absence of the proxy layer, and then try to emulate that on the server side of the connection.