Tennis, Perseverance, and DEF CON Challenges

In hacker culture, many people prefer to go by a handle. Frequently, that is done to preserve anonymity or to provide cover for work that might otherwise draw unwanted attention. At other times, the real identity behind the handle is well known and becomes a badge of belonging to the community. For example, it is widely known that Jeff Moss, the founder of Black Hat and DEF CON, is The Dark Tangent.

Today I am writing about DEF CON, the conference Moss created more than thirty years ago. It is a massive gathering that attracted more than 30,000 participants this year, and is loosely structured into topical “Villages.” For the past few years, my work team has provided significant content to the Aerospace Village. Our contribution centers around a highly coveted electronic badge that can only be obtained by winning one of a series of challenges. Each of those is intentionally designed to promote awareness of aviation and space cybersecurity. It is also aimed at building interest and skills in the next generation of engineers and researchers who are needed to create and sustain cyber-resilient aerospace systems.

This year, our team created fifteen different challenges for the Aerospace Village. Three of them were my design, rolled out under my handle, Synaptic Rodeo. My puzzles were deliberately crafted to be accessible to people of any background or knowledge level, whether they had deep technical expertise in cybersecurity and aviation or not. What these challenges did reward, however, were the traits that I believe are essential for long-term success in our field: curiosity, patience, and perseverance. A Synaptic Rodeo challenge never contains spoon-fed instructions but instead is about taking a vague clue and gradually eliminating possibilities until the correct solution emerges.

One challenge from this year illustrates that point. Participants were handed a paper stock notched key with the letters “N, E, S, W and some arrows on it. It took a couple of hours for a handful of people to figure out that the key could be overlaid on a sticker of nautical flags that had been pre-placed on one of the conference’s designated “sticker walls.” When lined up correctly, the notches revealed a phone number. Calling that number produced an audio message that recited phrases, which were in fact the alternate definitions of the flags within the International Code of Signals. In maritime tradition, a flag can signify both a letter and a phrase. For instance, the first phrase was “I want to communicate with you,” which corresponds to the letter “K.” That was the first letter in the final puzzle solution.

While it may seem strange to use nautical signaling in the Aerospace Village, the challenge was not out of place. This year’s electronic badge was an F-35 fighter jet, which is operated by both the United States Navy and the Marines. Maritime knowledge is therefore part of the broader aviation ecosystem. The puzzle also encouraged cross-pollination across DEF CON itself. Some players wandered into the Lock Picking Village because of the paper key. Others went to the Maritime Village to seek insight into the flags. In fact, the puzzle eventually drew a volunteer from the Maritime Village over to the Aerospace Village to investigate what was sending so many people over into their space. It turned out to be someone I had once worked closely with on the F-35 program. She now works in cybersecurity for the Coast Guard. In a convention of 30,000 people, that is a true small-world moment.

The paperstock key challenge was definitely more of a puzzle than a technical exercise. However, it mirrors the nature of the work my team performs every day. In aviation cybersecurity, we are always sifting through ambiguity and searching for vulnerabilities before our adversaries can find them. Success rarely comes from a straightforward, well-defined process. Rather, it comes from persistence and the ability to fight through uncertainty until the solution is found. The players who persevered and solved that challenge demonstrated qualities that are required for success in aviation system cybersecurity. Technical expertise can be taught, but persistence in the face of frustration is a more complex trait to cultivate.

Of course, there has to be a tennis connection. Otherwise, it wouldn’t appear on this site. The best players in the sport are not only technically skilled but also masters of perseverance. They problem-solve in real time, adapting to opponents, conditions, and pressure. Many matches are won through pure grit and determination. The same qualities that fuel a penetration tester working through an opaque security puzzle are the ones that carry a tennis player through the toughest matches.

Perseverance and problem-solving transcend domains. Whether in hacking, aviation, or tennis, those who thrive are the ones who face uncertainty head-on, keep moving forward, and eventually find a way to win.