Live-Fire Security Testing with Armitage and Metasploit

Your boss calls you into her office. You stare at the fake mahogany panels that line her wall. She strikes a match and asks, “Did you see the news? Criminals broke into our competitor's network. Embarrassing.” She lights her cigar and demands, “I want you to test our network and tell me that we're safe!”

Many are finding themselves in this position. The Payment Card Industry Data Security Standard requires a penetration test each year. Sarbanes-Oxley, FISMA and HIPAA demand an annual security review. Because of these pressures, many organizations are looking at penetration testing.

A penetration test is a step beyond a vulnerability assessment. A vulnerability assessment pairs missing patches and configuration errors with vague threat descriptions. A penetration test requires exploiting vulnerabilities to learn how an attacker may get access to key systems and files.

By following this article, you'll evaluate your security posture using the same process skilled attackers follow. You'll learn how to perform reconnaissance, exploit hosts and maneuver deeper into your network. To do this, you'll use Armitage and Metasploit.

Metasploit is an open-source exploit development framework owned by Rapid7. Armitage is one of the interfaces available for Metasploit. Armitage makes it easy to launch exploits and conduct post-exploitation steps once you have access to a host.

Use BackTrack Linux to follow this article. BackTrack Linux includes Metasploit and its dependencies. Update your Metasploit installation to get the latest version of Armitage:

cd /pentest/exploits/framework3
svn update .

To start Armitage:

/etc/init.d/mysql start
./armitage

Click Start MSF when the GUI comes up. Armitage will execute Metasploit in the background and connect to it.

Figure 1. Armitage User Interface

Figure 1 shows the Armitage user interface; it has three parts. The top-left is the module browser. Use this browser to search for and execute any of Metasploit's modules. The top-right is the targets area. Armitage displays your hosts here. The bottom is the tabs area. Armitage opens each shell, console and browser in a separate tab.

Attackers perform reconnaissance to learn your network configuration. Accurate information allows them to execute targeted attacks. Use reconnaissance to learn how attackers see your network. Attackers want to know which hosts are on your network, which ports are open and what software you're running.

Nmap is a popular reconnaissance tool. It scans your network to report open ports and service banners. Nmap also guesses host operating systems using irregularities in TCP/IP packet headers. Click Hosts→Nmap Scan→Quick Scan (OS Detect) to scan your network. Once the scan is complete, Armitage populates its targets area with your hosts. Click View→Targets→Table View to display your hosts in a table if you have a lot of hosts.

Right-click a host and select Services to see the results of your scan. Armitage displays the open ports and service banners in a new tab. Highlight multiple hosts to display your scan results in one tab. Figure 2 shows a scan of my network.

Figure 2. Network Services

Execute the reconnaissance step from both inside and outside your network. Outside reconnaissance will show you how attackers see your network. You'll learn what your firewall blocks and which services display too much information to anonymous users.

It's time to exploit your network. You need to match your hosts and services against Metasploit's 640+ exploits. The next sections in this article discuss automatic, semi-automatic and manual ways to do this. You also will learn how to launch password-guessing and client-side attacks.

I recommend using your inside scans for this phase of the penetration test. You should assume attackers will get inside your network perimeter. I also recommend attacking hosts from inside your network perimeter. This will better show what attackers can do. I justify these recommendations in the pivoting section.