“A boxer derives the greatest advantage from his sparring partner…”
— Epictetus, 50–135 AD

Hands up, chin tucked, and knees bent, the bell rings, signaling the start of the match. Both boxers meet in the center, circling each other, before Red throws out three jabs, feints a fourth, and lands a solid right hook on Blue. This isn’t Blue’s first match, but despite his rigorous training in front of the mirror, he feels the pressure. However, he soon realizes that the real challenge lies not in the punches, but in adjusting his defense to the opponent’s unpredictable moves.

Blue’s coach reassures him that his defense is not ineffective, but rather, it needs to be recalibrated. The coach explains that the only way to refine his defense is through real-time sparring, where he can test his skills against a live opponent. Similarly, in the realm of cybersecurity, having the right architecture, policies, and security measures in place is not enough. The true test of readiness lies in withstanding the pressure of a real attack.

The Difference Between Practice and the Real Fight

In the world of boxing, sparring partners are readily available, allowing fighters to hone their skills daily. However, in cybersecurity, the equivalent of sparring partners – penetration testing – is a rare occurrence, often happening only once or twice a year. This limited testing leaves security teams vulnerable, as they may not be adequately prepared to face real-world attacks.

The Consequences of Infrequent Testing

1. Drift: The Gradual Erosion of Defense

A boxer who goes months without sparring will likely experience a decline in their defensive skills. This phenomenon is akin to configuration drift in cybersecurity, where incremental changes in the environment can lead to gaps in defense. Over time, these gaps can become exploitable vulnerabilities, allowing attackers to breach the system.

2. Undetected Gaps: The Limitations of Shadowboxing

No matter how rigorous a boxer’s training is, it can never fully replicate the unpredictability of a real opponent. Similarly, in cybersecurity, no single pentesting assessment can identify every potential vulnerability. The only way to uncover these gaps is through repeated testing against real-world attack scenarios.

3. Limited Testing Scope: The Dangers of Partial Testing

A coach needs to assess their fighter’s skills against a variety of opponents to identify areas for improvement. In cybersecurity, testing against a limited range of threats can leave organizations exposed to other types of attacks. For instance, a web application may be secure, but a leaked credential or dubious API integration could still pose a significant risk.

Context Matters When it Comes to Prioritizing Fixes

Not every vulnerability is a critical threat. Just as a boxer’s unique style can compensate for technical flaws, compensating controls in cybersecurity can mitigate risks. In cybersecurity, vulnerability scanners often highlight numerous issues, but not all of them require immediate attention. The context of the IT environment is crucial in determining which vulnerabilities to prioritize.

The High Cost of Infrequent Testing

The value of testing against a real adversary is well established. However, the cost of traditional penetration testing can be prohibitively expensive, limiting the frequency of testing. This can lead to a situation where security teams only discover their vulnerabilities during an actual attack, resulting in devastating consequences.

Continuous, Proactive Testing

To effectively harden their defenses, organizations must move beyond infrequent annual testing. Instead, they should adopt continuous, automated testing that simulates real-world attacks. These tools can identify gaps, provide actionable insights, and offer precise fixes for remediation, all without the high cost of traditional testing.

By combining automated security validation with human expertise, organizations can maintain a strong defensive posture and adapt to evolving threats.

Learn more about automated pentesting by visiting Pentera.

Note: This article is a contributed piece from William Schaffer, Senior Sales Development Representative at Pentera.