An Interview with a Pentester - Real Penetration Testing Stories

Cybersecurity threats are growing more complex and dangerous every day. Organisations and individuals face an evolving threat landscape, from ransomware to insider threats. This is where penetration testing, or pentesting, plays a vital role. A skilled pentester simulates real-world attacks to identify security gaps before malicious hackers can exploit them. This blog is for anyone interested in cybersecurity: businesses, students, IT professionals and anyone looking to better understand the reality behind the scenes of cyber defence.

One of the most common vulnerabilities pentesters encounter is outdated software. Many organisations fail to apply patches quickly, leaving systems open to known exploits. For example, the infamous Equifax breach in 2017 occurred because of a failure to patch a known vulnerability.

Another frequent issue is weak authentication mechanisms. Many companies still use simple passwords or do not enforce multi-factor authentication. In one pentest engagement, a tester discovered that admin credentials were simply "admin123", giving them full access within minutes.

Social engineering also presents a major challenge. Pentesters often test employee awareness by sending phishing emails or making deceptive phone calls. In many cases, they can convince staff to reveal credentials or click malicious links. This shows that technical controls alone are not enough without proper user training.

To reduce these risks, organisations should adopt a layered approach to security. Regular vulnerability scanning and penetration testing should be part of the security lifecycle. This helps detect weaknesses early.

Implementing recognised frameworks such as Cyber Essentials or the NIST Cybersecurity Framework provides a solid foundation. These frameworks outline best practices for access control, patch management and incident response.

It is also crucial to maintain an updated inventory of assets. Knowing what you have helps you protect it. Applying security patches promptly and enforcing strong password policies with multi-factor authentication go a long way.

Security awareness training is another key component. Even the best technology can be undermined by a single click on a phishing email. Tools like KnowBe4, which simulate phishing attacks and train staff, are highly recommended.

Penetration testing is not just a checkbox exercise; it is a strategic necessity. In today’s threat landscape, attackers are not just script kiddies running tools. They are sophisticated cybercriminals, nation-state actors and insider threats with motives ranging from financial gain to espionage. Penetration testing gives organisations a controlled, safe way to discover how well they can withstand real-world attacks.

One of the most compelling reasons for penetration testing is risk identification and prioritisation. Not all vulnerabilities are created equal. Some may be low risk with little business impact, while others could result in data breaches, reputational damage or legal consequences. A pentest helps determine which vulnerabilities are most likely to be exploited and which could cause the most harm.

For instance, during a recent pentest engagement, an organisation believed their systems were well protected because they had implemented endpoint detection and response. However, the pentest revealed a misconfigured firewall that allowed unauthorised access from the outside. This oversight was caught in the pentest, allowing the organisation to fix it before an attacker could exploit it.

Penetration testing also supports regulatory compliance. Frameworks like PCI DSS, ISO 27001 and Cyber Essentials Plus require regular testing as part of an overall security programme. Failure to comply can lead to hefty fines or loss of customer trust. A certified penetration test not only strengthens your security but also proves due diligence.

Another critical reason is testing the effectiveness of your incident response. How quickly can your team detect, contain and recover from an intrusion? A pentest can include a red team simulation, where testers mimic advanced persistent threats (APTs) to evaluate how well your detection and response capabilities perform in real-time.

Furthermore, pentesting helps identify hidden or unknown vulnerabilities that may not be picked up by automated scanners. Many threats exist at the logic or configuration level — things like insecure session management, broken access controls or improper use of cryptographic functions. These require human expertise and intuition to uncover.

Equally important is its role in improving security awareness and culture. A post-pentest debrief is often an eye-opener for non-technical stakeholders. Seeing how easily a system can be breached, or how quickly a user falls for a phishing attack, drives home the message that cybersecurity is a shared responsibility.

Finally, penetration testing contributes to business continuity. Cyberattacks can cripple operations. Ransomware, for example, can halt production, lock critical systems and cost organisations millions in downtime and recovery. Pentesting enables businesses to identify weak spots before they become disasters.

When conducted regularly and integrated into the development lifecycle or infrastructure changes penetration testing becomes a proactive defence mechanism. It allows you to stay one step ahead of attackers, rather than reacting after the damage is done.

At Cybergen, we do more than just point out flaws. We help you understand them, fix them and prevent them from reoccurring. Our expert penetration testers provide detailed remediation guidance, mapped to your business goals. Whether you're securing cloud infrastructure, internal networks or customer-facing applications, penetration testing is a pillar of your cybersecurity posture.

At CyberGen Security, we deliver expert penetration testing tailored to your organisation. Our team of CREST-accredited testers simulates real-world attacks to identify and fix weaknesses before they are exploited.

We provide detailed reports with clear, actionable recommendations. Our approach is not just technical; we also offer strategic guidance to help organisations improve their overall security posture.

We empower users with knowledge and practical tools, including security awareness programmes, risk assessments and post-test support. Our services are designed to be both effective and accessible, helping clients meet compliance standards and protect their digital assets.

To give you a look behind the scenes, we interviewed one of our senior penetration testers to discuss the realities of the job, from tools and tactics to memorable moments in the field.

What does a typical day look like for a penetration tester?

Each day is different. One day I might be testing a cloud infrastructure, the next I could be simulating a phishing campaign. The job involves planning, execution and analysis. It requires a lot of creative thinking.

No two days are the same in the life of a penetration tester. A typical engagement might begin with a scope meeting, where the tester works with the client to define what systems or applications are in scope. The next step involves reconnaissance, collecting data on the target systems without triggering alarms.

Once that phase is complete, the tester begins actively probing systems for weaknesses. This could include testing web applications for injection flaws, scanning internal networks for outdated software, or identifying misconfigured firewalls.

Each test concludes with an in-depth report. But this isn’t just a list of technical jargon. Our pentesters translate complex findings into plain English, mapping vulnerabilities to business risks and providing clear recommendations.

What tools do you use regularly?

Some of the most-used tools include Burp Suite for web application testing, Nmap for network scanning and Metasploit for exploiting vulnerabilities. Each tool has its strength. The key is knowing when and how to use them.

Pentesters build their toolkit based on the type of engagement. While automated scanners are useful, much of the value comes from manual analysis and experience.

Here are a few key tools our pentesters rely on:

Burp Suite: A staple in web application testing. It intercepts and modifies HTTP traffic between browser and server.
Nmap: Used to discover hosts and services on a network by sending packets and analysing responses.
Metasploit Framework: A powerful platform for developing and executing exploits. It helps test vulnerabilities in a safe, controlled manner.
Wireshark: Network protocol analysis is critical, especially when looking into DNS poisoning or sniffing sensitive traffic.
Impacket: Useful for advanced Active Directory attacks such as NTLM relays and Kerberos ticket manipulation.

But beyond the tools, it's the tester’s mindset that counts most. Understanding the context, adapting on the fly, and thinking like an attacker are irreplaceable skills.

Have you ever discovered a vulnerability that shocked even you?

Yes, in one assessment, we found a backup folder on a public web server containing a ZIP file of the entire site’s source code and admin credentials. It was indexed by search engines, meaning anyone could have found it with the right search term. It highlighted just how easy it is for things to slip through the cracks.

What part of a Pen Test do you enjoy the most?

I love the challenge of privilege escalation. It’s like solving a complex puzzle, you start with very limited access and try to climb your way up to system or domain admin. When you finally get that access, it’s both satisfying and eye-opening for the client.

Do you ever feel conflicted about how easily people are manipulated?

Yes, especially with social engineering. It’s amazing how far you can get with a convincing tone of voice or a fake email signature. But it also reminds me why awareness training is so important. It’s not about blame, it’s about building resilience.

What misconceptions do companies often have about pentesting?

Many think it’s just running automated scans and generating a PDF. Real pen testing is much more in-depth. We think like attackers. We chain vulnerabilities together; exploit logic flaws and often uncover things automation simply can’t detect.

If you could fix one cybersecurity issue overnight across all organisations, what would it be?

Default passwords. It’s shocking how many internet-facing devices still use “admin/admin” or “password123.” It’s one of the easiest ways in, and it’s entirely preventable.

Any memorable stories from the field?

In one test, we found an exposed admin interface with no login protection. It allowed full control of a company’s customer database. They had no idea it was live on the internet. After our report, they immediately took steps to secure it.

Real-world penetration tests often uncover critical flaws that organisations had no idea existed. In one particular assessment, our tester discovered an admin portal accidentally exposed to the internet. Worse still, it had no login page, allowing unrestricted access. With just a browser, an attacker could have stolen thousands of customer records.

Another time, a staff member gave up credentials just because we called and said we were from IT. It shows how important user awareness is.

Finally, there was another internal test, a simulated phishing phone call (known as vishing) tricked a staff member into handing over their password. It served as a stark reminder that human error remains one of the biggest cybersecurity threats.

What advice would you give to someone entering the field?

Learn the basics thoroughly. Understand networking, operating systems and common vulnerabilities. Try platforms like Hack The Box or TryHackMe. And be curious. The best testers are always learning.

If you're looking to break into cybersecurity or move into offensive security, here’s what our pentester recommends:

Understand the fundamentals. Master TCP/IP, networking protocols, Linux and Windows environments. Everything in security is built on these foundations.
Learn the OWASP Top Ten. This list outlines the most common and dangerous web application vulnerabilities. Understanding these is essential.
Practice hands-on. Use platforms like TryHackMe and Hack The Box to build your skills in real-world environments.
Get certified. Qualifications like OSCP (Offensive Security Certified Professional), CompTIA PenTest+, and CREST Registered Tester are valuable benchmarks.
Be persistent and inquisitive. Many successful testers are self-taught. The mindset of constant learning, curiosity and lateral thinking is more important than memorising tools.

Penetration testing is a powerful tool for identifying and fixing security weaknesses before attackers strike. It is essential in a world where digital threats are constant and evolving.

Organisations cannot rely solely on firewalls and antivirus software. They need to understand where they are vulnerable and take proactive steps to secure their systems.

Cybergen Security offers expert guidance, hands-on testing and strategic support to help clients build resilient defences. Whether you are a business owner, IT leader or aspiring cybersecurity professional, now is the time to take action.