What came first — the vulnerability management program or the penetration test?

Penetration testing and vulnerability management are both critical components of a strong cybersecurity program — but they serve very different purposes. When organizations blur the lines between the two, they risk wasting valuable resources and missing out on the true value of a penetration test.

This article explores how a mature vulnerability management program can directly enhance the quality and impact of penetration testing. By removing low-hanging fruit and hygiene issues from the scope, organizations empower pentesters to focus on real adversarial simulation — the kind that reveals how attackers could truly compromise their environment.

Vulnerability Management vs. Penetration Testing: Know the Difference

Vulnerability Management (VM) is a continuous process that involves identifying, classifying, prioritizing, and remediating known vulnerabilities. It relies heavily on automated tools like Qualys, Tenable, or Rapid7 to scan systems for misconfigurations, outdated software, and known CVEs.

Penetration Testing, on the other hand, is a manual, time-boxed engagement where skilled professionals simulate real-world attacks. The goal is not just to find vulnerabilities, but to exploit them — chaining weaknesses together, escalating privileges, and moving laterally through the environment to uncover critical risks.

While there is some overlap in what both processes can uncover, the depth, intent, and value are fundamentally different.

Pentesters Reporting What Scanners Already Know

When vulnerability management is immature or nonexistent, pentesters are often forced to spend their limited engagement hours documenting issues that scanners could easily detect. These include:

·      Deprecated protocols like SSLv3 and TLS 1.0/1.1

·      Weak cipher suites

·      Telnet or FTP services exposed

·      SMB signing not enabled

·      Outdated software versions (e.g., Apache, PHP, OpenSSL)

·      Known vulnerabilities like Log4Shell

·      Missing security headers

·      Default credentials or open ports

These findings are valid, but they’re low-effort and high-noise — and they dilute the value of a penetration test. Worse, they consume time, resources and funds that could be spent on more impactful testing.

Pentesters Lose Their Edge

When pentesters are repeatedly tasked with identifying and analyzing basic hygiene issues, they lose valuable time — and more importantly, they risk losing touch with the advanced skills that define true offensive security.

Pentesters are specialists. They thrive on creativity, problem-solving, and adversarial thinking. But if they’re stuck documenting outdated protocols and weak configurations, they’re not practicing the techniques that matter most. Over time, they become less likely to remember that one obscure command or exploit chain — not because they aren’t capable, but because they aren’t challenged to use it.

True penetration testing involves:

·      Social engineering attacks against help desks or executives

·      Credential harvesting through phishing or password spraying

·      Privilege escalation via misconfigurations or kernel exploits

·      Lateral movement across systems and domains

·      Backdoor creation to simulate persistence

·      Discovery of sensitive files (e.g., plaintext passwords, config files, customer data)

·      Exfiltration of sensitive data— including the “holy grail” of domain admin credentials

These are the activities scanners can’t perform. They require creativity, experience, and time — and they provide real insight into how an attacker could compromise your environment.

When pentesters are consistently challenged to perform real adversarial testing, they build muscle memory, intuition, and speed. They become sharper, faster, and more capable — not just auditors, but true offensive security experts.

Let the Specialists Do What They’re Trained For

Imagine hiring a master mechanic to diagnose and repair a complex engine issue — but instead, you ask them to rotate your tires and change the oil. Sure, they can do it, but it’s not what they’re trained for, and it’s not where their value lies. Over time, if they only perform basic maintenance, they’ll lose touch with the diagnostic skills and intuition that made them exceptional in the first place.

The same applies to penetration testers.

If they’re constantly reporting on low-level findings that scanners can detect, they’re not practicing the advanced techniques that make them effective. They’re less likely to remember that one obscure command or exploit chain because they’re not using it often enough. But if they’re consistently challenged to perform true adversarial testing, they become sharper, faster, and more capable — building muscle memory and intuition that only comes from real-world practice.

“If your pentest reports come back full of outdated protocols, weak ciphers and misconfigurations... it’s time to ask: Are we using our vulnerability program effectively and are we wasting the pentesters' time?”

Ecosystem Maturity Enables Deeper Pentesting

Rapid7 documented two client scenarios that highlight how VM maturity impacts pentest outcomes:

1. Client A had poor VM hygiene — default root accounts, no segmentation, and unpatched systems. The pentest was limited to basic scanning and surface-level weaknesses.

2. Client B had strong VM practices — IAM roles, segmented networks, and cloud-native deployments. The pentesters were able to perform deep, chained attacks, simulate privilege escalation, and explore persistence tactics.

Key Takeaway: When baseline hygiene is in place, pentesters transition from superficial to sophisticated testing — delivering real adversarial insight and boosting overall security posture.

Read the full case study here:

After a mature VM program, pentesters' reports should be leaner, sharper, and far more valuable. Instead of listing outdated protocols, the report should detail how a real attacker could compromise the environment — and what controls failed to stop them.

Pentesters will have more time to:

·      Launch a targeted phishing campaign against help desk staff

·       Harvest credentials and pivot into internal systems

·      Escalate privileges using a misconfigured service account

·      Move laterally across segmented networks

·      Discover a plaintext password file with access to customer data

·      Simulate exfiltration and achieve domain admin access

Is Your Vulnerability Management Program Ready for a Pentest?

Before engaging in a penetration test, organizations should assess the maturity of their vulnerability management program. Here’s a quick checklist:

·      Do you run regular authenticated vulnerability scans across all critical assets?

·      Are deprecated protocols (e.g. ,SSLv3, TLS 1.0) already identified and remediated?

·      Is patch management automated and enforced across OS and third-party software?

·      Are weak configurations (e.g. ,SMB signing, Telnet, FTP) addressed proactively?

·      Do you have a process for tracking and resolving CVEs like Log4Shell?

·      Are findings from scanners triaged, assigned, and remediated within SLA?

·      Is there a centralized dashboard or reporting system for vulnerability status?

·      Do you have compensating controls for unpatchable systems?

·      Is your team trained to distinguish between scanner findings and pentest targets?

If you answered “no” to several of these, your pentesters may end up spending time on issues that should already be resolved — reducing the value of the engagement.

Stop the Overlap, Start the Impact

So… what came first — the vulnerability management program or the penetration test? It’s a fun question, but the answer matters more than you think.

Organizations that invest in mature vulnerability management programs get significantly more value from their penetration tests. They avoid paying skilled professionals to document weak ciphers and outdated protocols — things scanners can detect in minutes. Instead, they get deep, meaningful insights into their true risk posture.

When vulnerability management comes first, it clears the noise. It eliminates high-volume, low-impact findings and lets pentesters focus on what scanners can’t do: adversarial simulation, lateral movement, privilege escalation, and real-world compromise.

Allow scanners to scan and pentesters to hack.

Want better pentests? Start with better vulnerability management: Talk to Kudelski Security today.
Contact us here: https://kudelskisecurity.com/#contact-us

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