Cybersecurity Practices: Penetration Testers

November 15, 2025

Introduction

When the thought of a penetration tester as an occupation comes to mind, most people think of ethical hackers breaking through digital barriers and wreaking havoc on an organization, before pausing to help the organization remediate any discovered vulnerabilities. While this perspective is certainly quite entertaining, it tells only part of the story, as it fails to capture the nuances of the cultural and social landscape that penetration testers must be skilled to work within. Therefore, an argument can be made that the career of a penetration tester is fundamentally an applied social science due to its reliance on ethical social engineering, as penetration testers must work within an ethical framework to exploit human behavior and understand the sociology of an organization’s trust hierarchy. By exploring the daily routine of a penetration tester, social scientists can explore the ethical implications this work has on an organization’s employees and its internal social dynamics.

The Psychology of Human Vulnerability

When determining the initial attack vector to infiltrate an organization, it is usually quite clear to the attacker that a human vulnerability will be their most reliable avenue. This concept is famously summarized by security expert Bruce Schneier, who stated, “amateurs attack machines; professionals target people.” (Schneier, 2000). Schneier’s opinion is backed by concrete evidence from the 2025 Verizon Data Breach Investigations Report, which found that 60% of all data breaches involve the human element, including social engineering, errors, or misuse (Verizon, 2025). Therefore, it’s essential to investigate what makes human beings so vulnerable. Unsurprisingly, human psychology is to blame, and penetration testers study and apply it in their daily work. Social engineering attacks are effective because they exploit cognitive shortcuts and our natural tendency to trust, whereas a machine is not vulnerable to such social limitations. This is where the core concepts of the social sciences come into play, as an attacker has to leverage the principles of persuasion. A penetration tester may leverage the principles of authority by impersonating a boss or scarcity by pressuring the victim with a time-constrained task (Hadnagy & Fincher, 2015). Therefore, a large part of an effective ethical hacker’s plan is building attacks that target predictable psychological weaknesses in the human psyche instead of the technology itself.

The Social Fabric of an Organization

The work of a penetration tester relies on a sociological understanding of their target. In other words, the attackers must conduct thorough surveillance of an organization to best know how to exploit weaknesses in the organization’s hierarchy and culture instead of just the network and infrastructure. For example, when faced with an organization with a rigid, top-down hierarchy, a pen tester can exploit this social structure using a technique known as “pretexting.” According to Stu Sjouwerman, founder of the security awareness training platform KnowBe4, pretexting is defined as a fabricated scenario used to obtain information (Sjouwerman, 2020). While pretexting, an ethical hacker may impersonate a high-level executive who is angry or in a hurry to leverage the aforementioned social principle of authority. The idea is that such pressure overwhelms the target who would be responsible for regulating access, coercing them into complying with the demand and bypassing security procedures. In such an attack, no technical systems were exploited, and the attacker was able to use a human on the inside to gain access, representing a flaw in the social power structure of the organization instead of its cybersecurity infrastructure.

The Framework Behind Ethical Penetration Testing

With all of these nuances to consider, it’s important that penetration testers respect ethical boundaries while exploring the way threat actors disregard them. Unfortunately, the effectiveness of a penetration tester is limited by the rules of engagement, whether that be due to laws, company policy, or moral concerns. These rules function as a negotiated social contract, which itself is a sociological construct designed to manage the psychological impact on employees. These constraints, which are necessary to prevent harm and legal liability, mean that a tester’s simulation of an attack is inherently limited (Vertex Cyber Security, 2024). Therefore, it’s important for penetration testers to work with social scientists to determine what boundaries are acceptable when conducting a penetration test, and what advantages malicious hackers would have to operate outside of this framework (Baker, 2025). Simply put, ethical hackers should do everything they can to infiltrate an organization and discover vulnerabilities during their test without causing harm to employees.

Conclusion

It is clear that the skills required to be a penetration tester go beyond pure technical expertise. In reality, their profession is deeply integrated with the practice of applied social sciences. Through social engineering, penetration testers exploit vulnerabilities in human psychology, demonstrating that people are often the most accessible entry point into an organization. However, it’s also important that penetration testers operate ethically by respecting the fine line between a realistic simulation and the agreed-upon rules designed to keep employees and the organization safe from genuine harm. Ultimately, the role of a penetration tester exemplifies the intersection of technology, psychology, and ethics, illustrating that understanding people is just as crucial to cybersecurity as understanding machines.

References

Baker, G. (2025, November 13). Rules of Engagement Penetration Testing. FortifyFramework. Retrieved November 15, 2025, from https://www.fortifyframework.com/rules-of-engagement-penetration-testing/ Hadnagy, C., & Fincher, M. (2015). Phishing Dark Waters: The Offensive and Defensive Sides of Malicious Emails. Wiley. Schneier, B. (2000, October 15). Semantic Attacks: The Third Wave of Network Attacks. Schneier on Security. Retrieved November 15, 2025, from https://www.schneier.com/crypto-gram/archives/2000/1015.html Sjouwerman, S. (2020, June 10). Pretexting Defined. KnowBe4. Retrieved November 15, 2025, from https://blog.knowbe4.com/pretexting-defined Verizon. (2025, May 5). 2025 Data Breach Investigations Report 2025 Data Breach Investigations Report. Verizon. Retrieved November 15, 2025, from https://www.verizon.com/business/resources/reports/2025-dbir-executive-summary.pdf Vertex Cyber Security. (2024, August 13). The Limitations of Penetration Testing. Vertex Cyber Security. https://www.vertexcybersecurity.com.au/the-limitations-of-penetration-testing/