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Client Side Fingerprinting in Prep for SE

Reading time ~3 min

On a recent engagement, we were tasked with trying to gain access to the network via a phishing attack (specifically phishing only). In preparation for the attack, I wanted to see what software they were running, to see if Vlad and I could target them in a more intelligent fashion. As this technique worked well, I thought this was a neat trick worth sharing.

First off the approach was to perform some footprinting to see if I could find their likely Internet breakout. While I found the likely range (it had their mail server in it) I couldn’t find the exact IP they were being NAT’ed to. Not wanting to stop there, I tried out Vlad’s Skype IP disclosure trick, which worked like a charm. What’s cool about this approach is that it gives you both the internal and external IP of the user (so you can confirm they are connected to their internal network if you have another internal IP leak). You don’t even need to be “friends”,  you can just search for people who list the company in their details, or do some more advanced OSINT to find Skype IDs of employees.

Once I had that IP, I went on a hunt for web logs that had been indexed by a search engine, that contained hits from that IP. My thinking was that I run into indexed Apache or IIS logs fairly often when googling for IPs or the like, so maybe some of these contained the external NAT IP of the target organisation. It took a fair bit of search term fiddling, but in the end I found 14 unique hits from their organisation semi-complete with User Agent information (some were partially obscured).

This provided me with the following stats:

Operating System

Win XP      8

Win 7 32    3

Win 7 64    3


IE 8        8

IE 6        3

IE 7        1

IE 9        1


Win 7    IE 8     4

Win XP IE 8     4

Win XP IE 6     3

Win 7    IE 9     1

Win XP IE 7     1

Granted, it could be that the same machine was present in multiple logs and the stats are skewed, but they are a large enough organisation that I thought the chances were low, especially as most of the sites who’s logs I found were pretty niche. As validation of these results, later, once we had penetrated through to the internal network, it was clear that they had a big user base in regional offices still on Win XP and IE6, and a big user base at corporate offices who had been migrated to Windows 7 with IE8.

Unfortunately, the UserAgent didn’t make it clear whether they had Acrobat or Java or what versions they were at. We thought of using some JavaScript to do such detection, but were under a time constraint, and went with trying to pwn them instead, with the thinking that if it doesn’t work, we could retarget and at least get some debugging information.

Anecdotally, and to give the story an ending, it turned out that BlackHole and Metasploit’s Browser AutoPwn were a bust, even our customised stuff got nailed by Forefront when the stager tried to inject it’s payload at runtime, but an internal tool we use for launching modified meterpreter payloads worked like a charm (although, periodically died on Win7 64bit, so I’d recommend using reverse-http, you can restart sessions, and firing up a backup session to restart the other with).