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answers:

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I have an application server installed, listening for HTTP traffic on a port which is not blocked from the world by a firewall. I wish to expose the services offered by this application only through HTTPS, preferably as a "sub directory" of the HTTPS site already hosted by the server.

Using IIS7 Url Rewriting (as part of the ARR package), I am able to setup a rule that redirects all traffic to a sub path of my existing HTTPS site. However, I am facing some trouble, when trying to make the same rule route to my server farm setup - all requests matching the rule simply get 404 reponses. Adding the very same rule to a non-SSL site, yields the expected behaviour - the application services are proxied right trough.

What might be wrong in my setup? Is ARR proxying the HTTPS requests as HTTPS traffic to the application server? The application I want to host does not have a HTTPS interfaces so, if yes: can I tell it not to do so?

A: 

Yes, I can use IIS7/ARR to route HTTPS requests to HTTP application.

The problem I experienced, was caused by the fact that the web site I wanted to use as the "container" for the proxy directory was buildt with ASP.NET MVC. The URL routing framework within ASP.NET interfered with the IIS url rewriting, and causes the 404 error.

Jørn Schou-Rode