3:05 PM -- iPhones are sexy. If you don't think so, you haven't gotten to play with one long enough to realize it. Three of my coworkers have iPhones so far, and I'm finding something new every day that makes me want one. Coincidentally, my wife and I are currently searching for a new cellular provider, which recently brought up the topic of tethering the phone to a laptop for use as a modem.

During the discussion, Jordan, my coworker, found a video on YouTube showing how someone created an ad-hoc wireless connection between his laptop and the iPhone, and then used SSH as a SOCKS proxy for his laptop to connect to the Internet. Having used a Treo 650 for the last two years, I've used pssh to SSH into various servers, but never the other way. (For now, let's put aside the discussion of Apple's anti-unlocking measures and preventing third-party application installation.)

When the iPhone first came out, the security industry was busy shouting about the insecurity of the iPhone and concerns of data leakage. Now that HD Moore has begun adding support for the iPhone to the Metasploit Framework (MSF), there are two more threats enterprises need to be on the lookout for. (See Metasploit Adds iPhone Hacking Tools.)

First, all processes run as root (or administrator) which means that any exploited application means game over. Moore ported the bindshell and reverse-shell payloads to work on the iPhone architecture. In Metasploit, payloads are what get executed by the host after being exploited. The bindshell and reverse shells provide an attacker with a command shell on the remote system, which in this case, is an iPhone.

Now imagine if iPhone users in your enterprise like to use your wireless network. Suppose they open up a malicious email or Web page that compromises their iPhone over their cellular connection. That then would give an attacker a command shell, allowing the attacker to reach your internal network via wireless.

The second big risk is that now tech savvy, disgruntled users have a great mobile hacking platform that will go largely unnoticed by most people. It may look like that end user is "playing" with his iPhone in the hallway, but he may instead actually be breaching the CEO's desktop, or a network share containing some of your company's precious intellectual property.

Moore reports that Ruby is currently in a broken state on the iPhone, which prevents Metasploit 3 from running on it. But version 2 (written in Python) runs fine. I'm sure it won't take long to get fixed, and as soon as it is, let the hacking begin. Oh, and if you've not used Metasploit 3 recently (or ever), it currently has over 225 exploits and 110 payloads, making it something you should definitely research.

Scared yet? If not, then grab your wallet and get yourself an iPhone to see just how much damage you can do to your enterprise environment. You might be surprised. Oh, and when you're finished testing your iPhone, let me know and I'll send you my shipping address.

— John H. Sawyer is a security geek on the IT Security Team at the University of Florida. He enjoys taking long war walks on the beach and riding pwnies. When he's not fighting flaming, malware-infested machines or performing autopsies on blitzed boxes, he can usually be found hanging with his family, bouncing a baby on one knee and balancing a laptop on the other. Special to Dark Reading