OSEC

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SSL MITM not on port 443

christopher.rileyr-it.at
Date: Wed Aug 27 2008 - 06:32:32 CDT


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

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