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Have a IIS Reverse proxy redirect on specific request on WebSite with windows authentication and impersonation to another local site with win.auth + impersonation.

Reverse proxy and the web application placed on a different machines and iis versions (proxy- IIS 7.5 , webApp IIS6) and the same domain.

Requests through the reverse proxy does not allow the user to be authenticated on the remote server. has an infinite authentication request.

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This is inherent to the way windows authentication (NTLM) works: the password is never sent, authentication is done with a salted hash of the password, so the first server can authenticate the user but cannot re-use those credentials to impersonate the same user on a remote server (since without the password it cannot authenticate).
Look at this blog post to get more information about this problem (which is known as "double-hop problem").

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