We introduced the concept of Pen Testing 3.0 in our article on intelligence-led security validation. It’s an approach shaped by the gaps we kept seeing across client engagements.
Now, we show you how the model plays out in the real world. What happens when a client says, “We’ve done all the testing, we’ve got the reports, but we still don’t feel secure.”
What we do is less about scoping by habit and more about thinking together.
Fewer outputs. More uplift.
The problem with how pen testing is still done
As we’ve laid out in our guide to pen testing and our pen testing methodology explainer, most penetration tests are designed to appear successful but not to uncover how an organisation would actually be compromised.
They’re scoped to minimise disruption and timed for convenience. Rarely do they surface the gaps that matter or challenge core assumptions about architecture, access, or response.
You’re testing ‘A’. But the breach comes through B to Z.
The industry still obsesses over CVSS scores and vulnerability lists, but the real threats often come from misconfigurations, misunderstood trust relationships, and weaknesses in identity architecture. These don’t show up in most scans. They’re not in the PDF.
That’s the disconnect: a test that doesn’t reveal practical exposure or validate response under pressure isn’t helping.
From testing a scope to “working the problem”
At Chaleit, we start with one question: “What will get you hacked?”
It sounds simple, but it shifts everything.
Pen Testing 3.0 isn't scoped around systems. It’s shaped around what internal teams feel uneasy about, but can't yet prove. We ask, “What don’t you know?” That’s often where risk is hiding.
When a test is designed to validate what's already known, it becomes a performance. When it's designed to explore what feels unclear or uncomfortable, it becomes a tool for resilience.
“More” shouldn’t be the goal. It should be to find what matters most and to do something with it.
Your vulnerability scanner gives you 8,000 findings? We helped one client bring that down to 64 criticals and 16 real emergencies. That’s uplift.
What this looks like in practice
A client approached us with a common situation: a mature Azure environment, experienced security staff, and a decent testing history. But they couldn’t shake the feeling that something wasn’t right.
We didn’t start with a pre-written scope. We started with what they were unsure about.
Together, we:
Surfaced their assumptions
Mapped how identity and access actually behaved
Applied pressure across controls and architectural junctions
Instead of handing them a new stack of findings, we helped them clarify the risks that really mattered and gain confidence in their ability to address them.
Cyber security uplift
We’re not trying to replace tools, teams, or roadmaps. Our job is to verify whether it all holds together when it counts.
That means:
Asking contextual questions instead of blindly accepting a scope.
Collaborating with internal teams to interpret findings together.
Exploring systems, processes, and decisions (not just code).
We call it cyber security uplift. Not as a slogan, but as an operating principle. Testing should be part of how you improve, not just how you prove something.
Pen Testing 3.0 merges adversarial thinking with architectural understanding and collaborative execution.
Some might think this is a next-gen service tier. But it’s not that. It’s a shift in posture, from inspection to improvement.
Many security leaders already know where their weak spots might be. They just need a way to validate it, prioritise it, and act on it without getting lost in noise.
That’s what Pen Testing 3.0 does. It replaces “another report” with clarity, confidence, and outcomes.
Want to see what that looks like in your environment? Start with a security health check. It’s a quick process designed to avoid disruption, generate valuable insights, and create the basis for a real security uplift.
