The Laws of Stupidity and the Gaps in Your Security Posture

Carlo M. Cipolla, in his essay The Basic Laws of Human Stupidity, laid out a set of principles that are both hilarious and uncomfortably accurate when applied to everyday life. If you’ve ever watched a perfectly preventable security breach unfold and thought, “How did no one see this coming?” Cipolla has an explanation: stupidity—the kind that causes harm without benefiting anyone.

In security, stupidity isn’t just a human problem. It’s systemic. Your security posture is the sum of every decision you make—large or small, deliberate or “temporary.” Vulnerabilities don’t just happen; they’re created at the intersections of components and processes where decisions are made in isolation. And as Cipolla’s laws remind us, these decisions often externalize harm without yielding any real benefit to the decision-makers.

Cipolla’s Third Law states: “A stupid person is one who causes losses to another person or group of persons while deriving no gain and even possibly incurring losses themselves.” Unfortunately, this describes many decisions in security architecture. Consider a product team that ships a feature with hard-coded credentials because “it’s just for testing,” or an infrastructure team that approves open SSH access from anywhere because “we’ll lock it down later.” These decisions aren’t malicious, but they create cascading vulnerabilities that attackers are happy to exploit.

As Cipolla reminds us, the most dangerous kind of stupidity comes from ignoring the bigger picture. A classic example is teams measuring “success” by the number of CVEs closed or bugs fixed while ignoring metrics that actually reflect resilience, like lateral movement resistance or detection speed. It’s like polishing the hood of your car while leaving the gas tank open.

For a fun analogy, let’s turn to Star Wars. When the droids took over a ship’s trash system to gain access to more critical systems, they exploited what seemed like an insignificant component. As Adam Shostack highlights in his book Threats: What Every Engineer Should Learn from Star Wars, the trash system is a classic example of how attackers exploit overlooked parts of a system to achieve much bigger objectives. Security isn’t about protecting what seems important—it’s about understanding that any overlooked vulnerability can become critical. Whether it’s an unpatched library in your supply chain or a misconfigured process, attackers are happy to exploit your blind spots. If your trash system can sink your flagship, you’ve got bigger problems.

How do you avoid these mistakes? It starts by measuring the right things. Vanity metrics like “bugs closed” or “CVE counts” are security theater. They make you feel good but don’t tell you whether your system is truly secure. Engineers love optimizing for metrics—it’s in their blood. But optimizing for the wrong ones creates a false sense of security.

Instead, focus on metrics that reflect real resilience:

  • Lateral movement resistance: How hard is it for an attacker to move from one compromised system to another?
  • Detection speed: How quickly can you identify a breach? (And no, “when the customer calls” doesn’t count.)
  • Response effectiveness: Once detected, how quickly can you contain and neutralize the threat?
  • Minimized attack surfaces: How lean are your deployment images? Are you running unnecessary packages or services?
  • Key management hygiene: Are credentials rotated frequently? Are static secrets eliminated in favor of short-lived credentials?

These metrics focus on outcomes, not activity. While no single metric is sufficient, together they provide a clearer picture of how well security is embedded into the fabric of your organization.

Microsoft’s recent push to create division-wide Chief Security Officers is a good step toward addressing security silos. By embedding security leadership at the division level, they’re recognizing that vulnerabilities often arise between components, not just within them. But this alone isn’t enough. Security needs to be designed into the architecture itself, not just layered on as a management structure. It’s about ensuring every decision—from how APIs handle garbage inputs to how your CI/CD pipelines handle third-party code—is made with security in mind.

This is where proactive humility comes in: acknowledging that mistakes will happen, blind spots will exist, and systems must be designed to fail gracefully. Defense in depth isn’t just a buzzword—it’s an acknowledgment that your trash system will be attacked, and you’d better be ready for it.

Cipolla’s framework highlights a critical distinction:

  • Intelligent decisions benefit everyone—users, developers, and security teams—without externalizing harm. Think of secure defaults, automated safeguards, and least-privilege architectures.
  • Stupid decisions, on the other hand, create risk for everyone while providing no real gain. Hard-coded credentials, unnecessary privileges, or ignoring supply chain risks fall squarely into this category.

The challenge is to make intelligent decisions easier than stupid ones. This requires strong governance, effective tooling, and metrics that reward resilience over vanity. It’s not about avoiding mistakes altogether—that’s impossible—it’s about making it harder to make the big ones.

Cipolla’s laws might seem like a humorous take on human behavior, but they offer a sobering reminder of the gaps in security posture. Whether it’s overlooking the trash system in Star Wars or counting CVEs while ignoring systemic risks, stupidity in security is often the result of narrow thinking and poor measurement. The solution? Embed security into the fabric of your organization, focus on meaningful metrics, and foster a culture of proactive humility. By designing systems that make intelligent decisions easier than stupid ones, you can stop polishing the hood and start closing the gas tank.

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