Introduction

I have spent years watching how companies approach cybersecurity, and one thing has always struck me: penetration testing is often treated as a ritual rather than a meaningful exercise. Instead of being a powerful tool to uncover weaknesses, it has become a checkbox item for compliance, a way to say “we did it” without truly engaging with the results. In this article, I want to share my personal thoughts, experiences, and frustrations with how penetration testing is misused, why it fails when treated superficially, and how organizations can transform it into something genuinely valuable.

What Penetration Testing Really Means

Penetration testing, or “pen testing,” is supposed to simulate real-world attacks on systems, networks, and applications. The goal is to identify vulnerabilities before malicious actors exploit them. Done properly, it is a proactive measure that strengthens defenses.

But here’s the problem: many organizations don’t see it that way. They see pen testing as a requirement for compliance frameworks like PCI-DSS, HIPAA, or ISO standards. Instead of asking, “How can we learn from this?” they ask, “How quickly can we get this report and file it away?”

The Checkbox Mentality

I’ve seen companies schedule annual penetration tests just to satisfy auditors. The test is performed, a report is generated, and then it’s forgotten. No one follows up on the findings. No one integrates the lessons into their security strategy.

This checkbox mentality creates a dangerous illusion of safety. Executives believe they are secure because “the test was done,” but in reality, vulnerabilities remain unaddressed. It’s like getting a medical check-up, receiving a list of health issues, and then ignoring them because you already ticked the box that says “doctor visit completed.”

Why People Like Being Hacked

It may sound provocative, but I believe some organizations almost “like” being hacked. Not consciously, of course, but subconsciously they accept breaches as inevitable because they never take proactive steps. They rely on pen testing as a symbolic gesture rather than a genuine defense.

When a breach happens, they can say:

- “We did our pen test.”

- “We followed compliance.”

- “It wasn’t our fault.”

This mindset shifts responsibility away from leadership and onto the inevitability of cyberattacks. But the truth is, most breaches are preventable if organizations take pen testing seriously.

The Human Side of Pen Testing

As someone who has worked with penetration testers, I know they often feel frustrated. They uncover critical vulnerabilities, write detailed reports, and make recommendations. Yet, those reports sit unread in inboxes or are skimmed only for the executive summary.

Imagine being a doctor who diagnoses a life-threatening condition, only to have the patient say, “Thanks, but I’ll just wait until it gets worse.” That’s how many penetration testers feel.

Compliance vs. Security

Here’s a small table to illustrate the difference between compliance-driven pen testing and security-driven pen testing:

Real-World Example

I once consulted for a company that had passed its annual penetration test with “minor findings.” Six months later, they were breached through a vulnerability that had been listed in the report but never fixed. The breach cost them millions in damages and reputation.

When I asked why they hadn’t addressed the issue, the answer was simple: “We passed the test, so we thought we were fine.”

Why Pen Testing Fails

Penetration testing fails when:

- It’s too infrequent. Cyber threats evolve daily, but tests are often annual.

- Findings are ignored. Reports are treated as paperwork, not action plans.

- Scope is limited. Many tests only cover specific systems, leaving others vulnerable.

- Budget is misallocated. Companies spend more on passing audits than fixing vulnerabilities.

Making Pen Testing Valuable

If organizations want pen testing to matter, they need to:

1. Act on findings immediately. Don’t wait until the next audit cycle.

2. Integrate pen testing into strategy. Make it part of ongoing risk management.

3. Expand scope. Test not just networks, but applications, cloud systems, and employee practices.

4. Educate leadership. Executives must understand that pen testing is not just paperwork—it’s survival.

A Personal Reflection

I often ask myself: why do organizations resist taking pen testing seriously? The answer, I think, lies in human psychology. People prefer comfort over confrontation. It’s easier to believe “we are secure” than to face the uncomfortable truth that vulnerabilities exist.

But ignoring reality doesn’t make it go away. Hackers don’t care about compliance checkboxes. They care about weaknesses, and they will exploit them.

Supporting images

Here’s a simple illustration to show how organizations treat pen testing:

Instead, it should look like this:

Important Questions and Answers may you ask yourself:

Q. Why do companies treat pen testing as a checkbox exercise?

A. Because compliance frameworks demand it, and leadership often prioritizes passing audits over genuine security.

Q. Can pen testing alone prevent breaches?

A. No. Pen testing is a tool, not a solution. It must be combined with remediation, monitoring, and continuous improvement.

Q.How often should pen testing be done?

A: Ideally, continuously or at least quarterly. Annual tests are insufficient in today’s fast-changing threat landscape.

Q. What’s the biggest mistake companies make after a pen test?

A.Ignoring the findings or delaying remediation until the next audit cycle.

After reflecting deeply on this issue, I believe penetration testing has lost much of its intended value because organizations treat it as a checkbox exercise. They use it to satisfy auditors rather than to strengthen defenses. This mentality creates a dangerous illusion of safety, leaving systems vulnerable and organizations exposed.

The truth is, penetration testing is only as valuable as the actions taken afterward. A report sitting in a drawer does nothing to stop hackers. Real security comes from continuous improvement, proactive defense, and leadership that takes findings seriously.

If organizations want to stop “liking being hacked,” they must shift their mindset. Pen testing should not be about compliance—it should be about survival. It should be about learning, adapting, and protecting what matters most.

In the end, penetration testing is not a checkbox. It is a mirror that shows us our weaknesses. The question is: will we look into that mirror and act, or will we turn away and wait for the inevitable breach?