During a recent external pen-test, my teammate and I were able to gain root access to a Unix web server through a few serious application vulnerabilities. Once we had a reverse-shell going, we used wget to download Nmap, compiled it, and set off some scans to map out the DMZ and any reachable internal servers. Pretty straightforward so far.
Turned out that there really was no DMZ - everything was in one cloud behind their perimeter firewall. We quickly found a Class C containing lots of Windows hosts, including domain controllers and database servers, with all the expected ports open and exposed - jackpot! But we had a problem: the majority of our pen-testing tools for attacking Windows hosts only run on Windows, especially those related to MS SQL server. We couldn't run them on our compromised Unix server, and we didn't have the time to hunt down and test any equivalent tools that might exist for *nix platforms.
What we needed was a way to securely tunnel a connection from our pen-test system, through the Internet to the compromised Unix web server, and then ultimately to the Windows hosts behind the firewall. Something like stunnel first came to mind, but their firewall would block our inbound connection attempt.
This wonderful tool, available for both *nix and Windows, lets you set up an encrypted two-way tunnel for TCP or UDP connections. But the real beauty is that you can initialize a "reverse tunnel", much in the same way you'd use netcat to set up a reverse shell and bypass firewalls that strictly filter inbound connections. We configured our pen-test system to be the client and listen for connections from the Zebedee server. We then installed and ran Zebedee's server component on the compromised Unix host, and set up an outgoing reverse tunnel to our listener. The outbound connection got through their firewall, and we were able to directly attack the internal Windows servers from our own machine. You just point your testing tools to localhost as the destination IP, and to the port on which Zebedee client has established the tunnel. (As you might imagine, explaining how this worked to non-technical folks at our client was rather difficult).
Needless to say we were extremely happy to get this working, especially because it took quite a long time to configure and set up properly. Some of the documentation was confusing, and we kept having silly compilation issues because dependencies were in the wrong path. One noteworthy problem we ran into is that we could only get the server to tunnel to one endpoint at a time. In other words, our client listener could stay open, but we had to re-initialize the server with a different tunneling endpoint specified on the command line each time we wanted to test a new Windows host.
Ultimately, that limitation wasn't a huge deal - we still were able to eventually compromise a key Windows server - it just took some extra time to do the testing. The documentation indicates that you can set up a tunnel to any number of endpoints, so we'll have to figure that out for our next pen-test.
Despite these minor quibbles, Zebedee is a great tool that is invaluable for external pen-tests, particularly when your system compromises have spilled over into protected networks.