Legacy point-in-time penetration testing started in the 1960s, back when networks were static, attackers behaved like hobbyists, and change moved slowly. We live in a very different world now.
The practice of annual testing was shaped for a world that no longer exists, one without dynamic cloud infrastructure, identity sprawl, or AI-accelerated threats. Yet many still rely on it as their primary method to “validate” security, even though it fails to match the speed, complexity, and creativity of modern adversaries.
The Limits of Annual Testing
True offensive insight should drive every defensive action, helping security leaders allocate resources, justify budgets, and tighten posture where it matters most. But the annual pen test rarely offers that context. Point-in-time testing usually delivers more optics than outcomes.
Many position annual pen tests as a form of assurance.
But validation without context doesn’t equal assurance; it simply becomes ritual.
A ritual that identifies the vulnerabilities you have today while leaving tomorrow to chance. And while annual pen testing may satisfy auditors, it won’t stop adversaries.
Environments shift, new assets spin up, configurations drift, and identity sprawl grows. By the time a penetration test engagement ends and the report lands, it no longer reflects today’s risk, it only captures a snapshot of yesterday’s environment.
So, while compliance asks: Are you checking?
Offensive security asks: Can you withstand real adversarial pressure today? Isn’t that the point of all the investment in defensive technology and process?
The bigger issue isn’t just outdated methods, it’s a fundamental misalignment around the purpose of offensive security. Too often, people see it as a testing function, a way to check for exposures. But the art of offense goes beyond finding issues; it uncovers issues in context. It pressure-tests assumptions, surfaces real attack paths, and exposes how defenses hold up against relentless attacks. Ultimately, it proves whether the huge investment in defense works.
Done right, offense doesn’t create noise. It creates clarity, a lens that reveals what’s exploitable, what’s resilient, and where material risk exists inside an organization.
That’s why a true offensive partner doesn’t chase more data. They focus on actionable context. Most enterprises already have visibility. What they lack is prioritization: how attackers can chain exposures, how they actually move, and how to stay one step ahead with confidence. The power of modern offensive security doesn’t come from the volume of findings. It comes from delivering proof of exploitable risk that sharpens real-world decisions.
Why Continuous Offense Matters
Time-over-target matters. Continuous offensive pressure uncovers the everyday realities that combine to form exploitable paths.
That’s why we built Chariot, to make continuous offensive security actionable.
We don’t just surface exposures. We prove what’s exploitable, map how attackers move, and help you harden defenses before they’re breached. With that context, you can prioritize spend, tighten controls, and protect your most valuable assets.
Offensive insight shapes defensive posture.
Conclusion
Annual pen tests deliver snapshots of yesterday. Continuous offensive security delivers clarity today. That clarity is what lets security leaders prove resilience, prioritize investment, and keep pace with real adversaries.
And you don’t have to take our word for it. Erik Hart, CISO of Cushman & Wakefield, recently shared why his team shifted from annual penetration testing to a continuous approach and what it means for building a modern defense strategy.
