Security War Games

Let's face it: Protecting your technical environment from internal and external attacks isn't much different than the age-old wars fought since mankind picked up a rock. The goal is to keep people in and/or keep people out. Just much less blood.

How are you preparing your Blue Team from getting decimated on the virtual battlefield? With training and drills? Has that approach been effective?

When it comes to information security, I've always found the "traditional" classroom-based training difficult to retain and recall at a moment's notice unless it was a hands-on exercise. Adding in a spice of entertainment piques interest and retention for the next round of content.

Update: A reader caught my bad math. Windows NT 4 RTM was released July 1996. It was closer to 16 years ago. I recall 19 years ago sitting through a Microsoft Windows NT 4 week of training that was content-rich but lacking flavor. Nonetheless, the most memorable portions were when we attacked each other systems. What we did was remotely made some environment changes and then executed WinNuke to BSOD the box using of the Out-Of-Band TCP port 139 exploit. The challenge was to quickly find and undo the antagonistic setting changes in order to keep up with the instructor's lesson.

Oh, I forgot to mention that we did this without the instructor's knowledge.

I barely recall other lessons the instructor presented, but I will never forget how we educated each other through unsanctioned war games.

Our brains haven't evolved enough during the past 16 years to change how it stores data, but our wisdom has.

The security communities have transformed the military-based training exercises of Capture The Flag (CTF) into the world of technology. CTF isn't new, but it's gaining momentum as a complement to the traditional classroom-based training we've grown to love.

Applying knowledge gained from classroom, books, or online sources to a series of hands-on challenges that are forcing one to think differently reinforces that knowledge. Challenges that are fun, engaging, and competitive are when education happens and the content moves into long-term memory. Learning happens.

The reward system for the participant is immediate gratification by finding the flag, earning points, watching the ranking elevate, and hoping to take home a prize while getting better. The benefit for an organization is a lower cost for education with a higher retention rate! Who wouldn't want that?

During your next incident, would you rather spend a direct cost to an external company or have better educated staff who can think outside of the box any time of day?

Not all CTFs are created equally. Some CTFs may be specific to individuals attempting a social engineering attack, while others are team-based attacks and defend challenges or emulate the TV show Jeopardy. CTFs will challenge one's skills in the areas of Web application security, forensics, reverse engineering, network sniffing, cryptanalysis, system administration, programming, and several other disciplines.

Some readers of this article may feel that CTFs are dark activities done late at night for the extremists and not the IS professional. Completely not true. People from all walks of life with a passion to beat the challenges, alone or as a team, will participate.

The annual DEF CON CTF draws competitors from all over the world and is difficult to get past the qualifiers. Someone curious about participating in a CTF for the first time can attend a conference such as BSides. BSidesChicago and BSidesDetroit are currently hosting the first-ever cross-conference and cross-city CTF spanning a couple of months. BSidesDenver will be hosting a Jeopardy-style CTF starting on May 24.

Having difficulty getting out of the office (even on weekends) and want to pop an operating system during a CTF? You may want to consider joining the team-based attack and defend online war game called CTF365. Simply create an account, join/create a team, and build your fortress. Keep your fortress safe while attempting to penetrate a fortress in another country.

Perhaps CTF365 is the international training ground for cyberwarfare?

Still not convinced that a CTF will test your metal, some security organizations offer fun challenges in the way of puzzles, such as Naked Security's sophospuzzle.

I would like to end with these thoughts: Security is everyone's responsibility, from the person sweeping the floor all the way up to signing the checks. When the cyberwar comes, if we ever find out what cyberwar means (as recently outlined by Corman and Jericho at THOTCON), your staff will be the soldiers on the front line.

Get your soldiers ready.

No security, no privacy. Know security, know privacy.

David Schwartzberg is a Senior Security Engineer at Sophos, where he specializes in latest trends in malware, web threats, endpoint and data protection, mobile security, cloud and network security. He is a regular speaker at security conferences and serves as a guest blogger for the award winning Naked Security blog. David talks regularly with technology executives and professionals to help protect their organizations against the latest security threats. Follow him on Twitter @DSchwartzberg