For many organisations, penetration testing is still treated as an annual checkbox exercise. It’s scheduled, scoped, completed, and filed away until next year. But as cyber risk continues to rise and environments change faster than ever, this point‑in‑time approach leaves critical gaps that attackers are more than happy to exploit.
So what isn’t your pen test telling you?
Pen Testing vs Vulnerability Management: Different Lenses, Different Value
Vulnerability scanning plays an important role in identifying missing patches, outdated software, and known weaknesses across your environment. But it only tells part of the story. Pen testing adds a different and essential perspective: how those weaknesses can actually be chained together and exploited by a real attacker.
The key difference is mindset. Defensive teams focus on protecting systems; attackers focus on finding the easiest path in. A traditional pen test helps bridge that gap, but only for a snapshot in time.
The Problem with Annual Testing
Modern IT environments aren’t static. New offices open, cloud services are added, temporary configurations are made, and acquisitions bring unfamiliar infrastructure into the mix. An annual pen test can’t account for these constant changes.
Common issues often appear after the test is complete:
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Default passwords left on temporary devices
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Overlooked systems like CCTV or access control platforms
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IPv6 enabled by default, but never secured
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Misconfigurations introduced during routine changes
Attackers don’t care about test scope or timing. They care about opportunity.
Overlooked Risks Hiding in Plain Sight
Some of the most frequently missed weaknesses aren’t advanced zero‑day exploits, but simple, well‑known issues. IPv6 is a prime example: many organisations secure IPv4 extensively, while forgetting that IPv6 is enabled on most devices by default. That blind spot can allow man‑in‑the‑middle attacks with little resistance.
Email security is another major gap. DMARC, DKIM, and SPF records are often implemented incorrectly, or set to “monitor only”, giving a false sense of protection. These settings are publicly visible and are actively reviewed by attackers looking to impersonate trusted brands and bypass technical controls with social engineering.
When Patching Isn’t an Option
Not every vulnerability can be fixed. Legacy systems, operational technology, and business‑critical platforms often can’t be upgraded without significant disruption. In these cases, detection becomes just as important as prevention.
Deception technologies, such as honeypots or decoy systems, can act as early warning signals. By replicating known vulnerabilities in a controlled way, they alert teams the moment an attacker starts probing, giving defenders a chance to respond before real damage is done.
The Human Factor Still Matters Most
Many of the most serious breaches don’t start with technical exploits at all. They begin with people. Phishing, MFA fatigue, service desk manipulation, and insider misuse all bypass traditional security tooling because the activity looks legitimate.
This is where approaches like grey‑box testing and continuous “hacking‑as‑a‑service” models add value. By simulating what happens when valid credentials are compromised, organisations can see how far an attacker could really go, and fix misconfigurations before they’re abused.
From Point‑in‑Time to Continuous Visibility
The key takeaway is simple: security isn’t about one test, one report, or one moment. It’s about consistent visibility and prioritisation. Automated and repeatable testing doesn’t replace manual pen testing, but it complements it, reducing noise, catching change‑driven risk, and helping stretched IT teams focus on what truly matters.
Because the most dangerous thing your pen test might be telling you… is that everything looks fine.
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