True Stories of the TRC-Web Application Security

HackerKombat II: Capturing Flags, Pursuing the Trophy

Years ago, a small group of 5-6 of us at WhiteHat held impromptu hacking contests – usually over lunch or during breaks in the day – in which we would race each other to be the quickest to discover vulnerabilities in real live customer websites (banks, retailers, social networks, whatever). No website survived longer than maybe 20 minutes. These contests were a nice break in the day and they allowed us to share (or perhaps show off) our ability to break into things quickly. The activity usually provided comic relief, moments of humility, 🙂 and most importantly they opened opportunities to learn from each other.

We have scores of extremely talented and creative minds working at WhiteHat and these activities were some of the earliest testaments to that. Our corporate culture is eager to break what was previously thought of as “secure,” often just for the fun and challenge. Today, WhiteHat has more than 100 application security specialists in our Threat Research Center (TRC) alone – essentially our own Web hacker army. With so many people now, our contests were forced to evolve, to grow and to mature. We now organize a formal internal activity called HackerKombat.

HackerKombat is a WhiteHat employee only event, a game we hold every couple of months, a late-night battle between some of the best “breakers” in the business. HackerKombat is our version of a “Hackathon,” which companies like Facebook and others host as a means to challenge their engineers to build cool new apps, new features, etc.


HackerKombat challenges our team to break things — to break websites and web applications, to test our hacker skills in a pizza and alcohol infused environment. The goals are to have some fun in a way that only hackers could appreciate, but also to encourage teamwork and thinking outside the box, and to expose areas of knowledge where we are weak.

Unlike years past, the websites and applications we target are staged – no more hacking live customer sites! We have learned that while the average business-driving website might withstand the malicious traffic of a few hackers targeting it, a dozen or more could easily cause downtime. We certainly can’t have that and you’ll see how easy that can be later in this post.

The HackerKombat challenges are designed by Kyle Osborn (@theKos), a WhiteHat TRC alumnus, accomplished security researcher, and frequent conference speaker, who is currently employed by Tesla Motors. Challenges are also developed by current TRC members, but doing so disqualifies them from actually playing — gotta keep things fair as we can. This isn’t much in way of rules for HackerKombat. I mean, are hackers expected to follow them anyway? 😉

Today, finding a single vulnerability is nowhere near enough to claim victory. HackerKombat is a series of challenges that are very difficult and require a wide variety of technical ability. Defeating every challenge requires a great team, and great teamwork. No way can a single person, even the best and brightest among us, get through every challenge and expect to have any chance of winning. Past events have shown there is strength in numbers – so we also had to cap the team size at 5-6 to keep things even.

A few weeks ago we hosted the second formal event – HackerKombat II. Teams were decided by draft, for a total of six teams with five combatants each spanning our Santa Clara headquarters as well as in our TRC location in Houston. In the hours leading up to HK II the trash talking was constant and searing. There was even an office pool posted and people were placing bets on the winning team! The biggest prize of all: our custom trophy.


The exact moment the game began the trash-talking ceased, poker faces were set – chatter became eerily quiet. If you wanted to win, and everyone did, every second and key press mattered. If someone was active on Jabber (chat client), you knew they were stuck. 😉

Each team’s approach to the 10 challenges was probably different. For my team – “Zerg” – we assessed each by triaging them first: determining what skill sets it would take and assigning those tasks to the right team member to tackle.  The first 4 challenges or so were completed fairly easily within the first hour. The next 2-3 challenges we had to pair up to defeat them. Writing some code was necessary. Another hour gone. Then things got hard, really hard, and every team’s progress slowed way down.

Some of the challenges posed interesting hurdles that the designers did not anticipate. For instance, one challenge required teams to run DirBuster, which brute-forces web requests looking for a hidden web directory. The problem, however, is that a single Apache web server is not used to handling a dozen people all doing the same thing and sending thousands of requests per second. The challenge server died. Remember how I mentioned downtime? Apparently, speed in capturing that particular flag was the winning skill because no other team could get in to tackle it! Argh!

For the most difficult challenges, 9 and 10, Zerg had to gel together as a team to try to figure out the best approach and make incremental gains. I’m clearly very weak in my steganography skills. Terribly frustrating at a time we were so close to victory, but couldn’t seal the deal. An hour of study beforehand would have been enough.

In the end, the winning team –  “Terrans” from Santa Clara – prevailed by completing all 10 challenges and capturing all 12 flags in a time of 4h and 46min, barely edging out the team in Houston – “PurpleStuff” – which came in second at 4h and 49min. Yes, when it was all said and done, 3 minutes separated the leaders. Imagine that!

In another moment of humility, Robert Hansen (@RSnake), another “great” in the industry, can at least claim he beat me and came in second. 🙂 I’m not exactly certain even now where my team placed, probably around 4th, as every team managed to capture at least 10 flags before the Terrans claimed ultimate victory.  I congratulate Rob, Nick, Dustin, Jon Paul and Ron for their win.

All in all, HK II was fun for all involved and everyone learned a great deal. We learned new techniques that the bad guys can use in the wild, and we learned where each of us individually needs to brush up on our studies. HK II’s success makes a founder very proud. I’m sure there are few, if any, companies that can pull off such an event.

 I look forward to HK III. I want that trophy!

[Check out photos from JerCon and HK II here.]