Legacy point-in-time penetration testing was first implemented in the 1960s, back when networks were static, attackers were hobbyists, and change happened slowly. We live in a very different world now.
The practice of testing annually was shaped for a world that no longer exists; one without dynamic cloud infrastructure, identity sprawl, or AI-accelerated threats. And yet, it remains the primary go-to method many organizations use to “validate” their security despite being fundamentally misaligned with the speed, complexity, and creativity of modern adversaries.
True offensive insight should inform every defensive action, helping security leaders allocate resources, justify budget, and tighten posture where it matters most. But the annual pen test rarely provides that level of context. Point-in-time testing typically delivers more optics than outcomes.
Annual pen tests are often positioned as a form of assurance.
But validation without context isn’t assurance, it’s ritual.
A ritual that identifies the vulnerabilities that you have today, while leaving tomorrow up 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 an annual pen test engagement ends and the report lands, it’s no longer a reflection of today’s risk it’s a snapshot of yesterday’s environment.
So, while compliance asks: Are you checking?
Offensive security asks: Could you withstand real adversarial pressure today? Isn’t this the whole point of all the investment in defensive technology and process?
The bigger issue isn’t simply outdated methods; it’s a fundamental misalignment around what the purpose of offensive security. Far too often, it’s seen as a testing function; a way to check for exposures. But the art of offense isn’t about finding issues, it’s about understanding them in context. It’s about pressure-testing assumptions, surfacing real attack paths, and exposing how defenses hold up against relentless attacks. Ultimately, it’s about knowing that the huge investment you’ve made in defense is working.
Done right, offense isn’t noise. It’s clarity. A lens that reveals what’s exploitable, what’s resilient, and where the material risk lies within an organization.
That’s why a true offensive partner isn’t focused on more data, they’re, focused on actionable context. Most enterprises already have visibility. What they need is prioritization: how exposures can be chained, how attackers move, and how to confidently stay one step ahead. The power of modern offensive security isn’t in the volume of findings, it’s in delivering proof of exploitable risk that sharpens real-world decisions.
And time-over-target matters. Continuous offensive pressure exposes the everyday realities that combine into 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. So you can prioritize spend, tighten controls, and protect your most valuable assets.
Offensive insight influences defensive posture.
Attackers don’t care when your next test is scheduled.
They’re already moving.
