SSL MITM not on port 443

[christopher.riley () r-it at]

I've come across a problem in a pentest that I'm working on right now that 
I thought the members of the list might be able to assist me with.

I'm working with a propriatary software (written in C++) that communicates 
on a high port number using HTTPS. I'm trying to test to see if the 
software can be fooled into accepting a false certificate and then traffic 
decoded into clear text.

So far I've tried Ettercap, webmitm and CAIN without much luck. The 
closest I can get is Ettercap capturing the communication, however it 
doesn't offer a forged certificate and all captured traffic is still 
encrypted using the normal server certificate. Not  much of a MITM attack. 
I've confirmed that Ettercap works as advertised against a couple of sites 
in Internet Explorer and all seems to work normally.

Does anybody know of a way to force Ettercap to perform an SSL mitm even 
though the port isn't associated with HTTPS ? or maybe you can suggest a 
better tool for the job ? I can control where the application looks for 
the server, so I can divert it through some kind of forwarding proxy if 
needed ?

Thanks,

Chris Riley

----------------------------------------
Raiffeisen Informatik GmbH, Firmenbuchnr. 88239p, Handelsgericht Wien, DVR 0486809, UID ATU 16351908

Der Austausch von Nachrichten mit oben angefuehrtem Absender via E-Mail dient ausschliesslich Informationszwecken. 
Rechtsgeschaeftliche Erklaerungen duerfen ueber dieses Medium nicht ausgetauscht werden. 
Correspondence with above mentioned sender via e-mail is only for information purposes. This medium may not be used for 
exchange of legally-binding communications.
----------------------------------------


------------------------------------------------------------------------
This list is sponsored by: Cenzic

Top 5 Common Mistakes in 
Securing Web Applications
Get 45 Min Video and PPT Slides

www.cenzic.com/landing/securityfocus/hackinar
------------------------------------------------------------------------