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Re: NTLM and man-in-the-middle proxies not working

Subject: Re: NTLM and man-in-the-middle proxies not working
Date: Tue, 20 Sep 2005 13:45:03 -0700
That isn't 100% true.  Because NTLM authenticates a TCP connection,
not a web request, a proxy must specifically support NTLM
authentication proxying or bad-things might happen.  To show IE that
this is supported the proxy must set the following header if
WWW-Authenticate header exists:

Proxy-Support: Session-Based-Authentication

this isn't well documented which is why most MITM proxies didn't
support NTLM for a long-ass time.

mike

On 9/19/05, Amit Klein (AKsecurity) <aksecurity@hotpop.com> wrote:
On 19 Sep 2005 at 10:52, Eoin Keary wrote:

I find Burp works well for MITM stuff


With IE and NTLM? What version (maybe an old one)?

The phenomenon I was talking about was actually observed 4 years ago.

From a Squid-Dev posting by Chemolli Francesco (USI), Mon, 20 Aug 2001
(http://www.squid-cache.org/mail-archive/squid-dev/200108/0152.html):

"It is worth noticing that recent version of MS Internet Explorer
WILL NOT EVEN ATTEMPT to perform NTLM authentication if a proxy
is in use to reach the destination host."

And I also verified this on IE 6.0 SP2 (WinXP SP2).

-Amit

On 16/09/05, Amit Klein (AKsecurity) <aksecurity@hotpop.com> wrote:
On 15 Sep 2005 at 15:42, raymond_b_jimenez@yahoo.com wrote:


Most interesting is the fact that IE passes IWA credentials over a 
proxy. I had put in a demo environment, and I did sucessfully manage to 
use IE/IWA through a proxy (in this case Odysseus). Just in case, I 
tested it again and it does pass IWA through proxy.


Weird. I double checked (this time I used Odysseus, 2.0B10), but no good, 
my IE
(6.0.3790.0) doesn't even ask me for the NTLM credentials when it's 
configured with a
forward proxy. What's your IE version? Can other people check this please?






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