What Your Pentest Isn't Telling You

What Your Pentest Isn't Telling You

What Your Pentest Isn't Telling You 1200 630 Andrew Heller

Many organizations believe they are secure because they have passed a penetration test. However, most penetration tests do not accurately reflect how attackers actually behave. They are constrained by scope, timing, and the rules of engagement. They produce a report, but they do not simulate a real-world threat.


Penetration testing is useful for identifying known vulnerabilities in specific assets and systems, but it is not designed to answer broader questions:

  • Can an attacker move laterally once inside?
  • Can they persist undetected in cloud infrastructure?
  • Would your team detect a low-and-slow exfiltration over trusted channels?

Red Teaming is not a fancier pentest. It is a mindset shift. It assumes compromise and asks, "Now what?"

Red Teams simulate real adversaries using a blend of technical, physical, and social methods. They look for paths to impact. They operate quietly. They prioritize outcomes over alerts.

And that is just the beginning.

Purple Teaming turns Red Team insight into defender action. It is not a postmortem. It is a live, collaborative engagement. Detection engineers and threat hunters work directly with adversarial operators to:

  • Tune telemetry
  • Build detection logic
  • Strengthen containment processes
  • Shorten response timelines

The value is not in the finding. It’s in what your team learns, builds, and improves during and after the test.


To shift from a pass/fail mentality to a readiness mindset, you need:

  • Realistic attack simulation
  • Real-time defender engagement
  • Post-engagement metrics that measure improvement

Pentests identify static flaws. Red and Purple Teaming expose dynamic risk.

If your security validation ends with a PDF, you are not testing reality. You are testing paperwork.

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