On April 22, 2025, Insight Assurance hosted a webinar. Rochelle Sikhovski moderated a discussion with Dr. Marwan Omar, Chief AI Officer at Insight Assurance, and Dan Le, CEO and CISO of RED Cup IT. The topic was penetration testing, why it matters, and what some strategies are to get the most out of it.
What Is Penetration Testing and Why Is It Critical?
Penetration testing involves the purposeful attempt to break into networks to find vulnerabilities, security flaws, bugs, and backdoors. These tests simulate real-world attacks designed to find weak points before threat actors do. Depending on the objective, penetration tests may be black-box (no internal knowledge), white-box (full access), or gray-box (partial access), simulating different types of attackers. In fact, during the webinar, Dr. Omar stressed that hackers are already testing your security. Cyberattacks are becoming faster, more frequent, and harder to detect. This only raises the importance of penetration testing (or pentesting, for short).
Le mentioned a real-world story that illustrates the value of pentesting. He described a physical test—looking for ways to infiltrate a property. While some were focused on the lock and key, the test revealed a gap in the fence that people could simply walk around. This shows how people can be too ‘in the weeds’ in their own business; seeing it as an outsider can reveal something obvious, yet overlooked.
Penetration testing, virtual or real, addresses and remediates these issues before attackers exploit them. This often requires thinking like hackers and understanding the tools, techniques, and tactics they use.
Compliance, Regulations, and Pentesting Frequency
Numerous compliance frameworks require penetration testing — including SOC 2, PCI, and ISO 27001 — but meeting these guidelines alone doesn’t guarantee secure environments. Most frameworks recommend annual penetration testing or testing after significant system changes. However, frequency should reflect your threat model and risk appetite. Some vulnerabilities can only be discovered through active exploitation attempts, something that automated tools or checklists often miss.
Security tools such as antivirus software and firewalls provide baseline defense but often rely on known threat signatures. Penetration testing reveals unknown, exploitable vulnerabilities — including logic flaws and misconfigurations.
Dr. Omar mentioned many clients think compliance is a formula. For example, if an organization complies with a framework, then that automatically means it’s safe. But this simply isn’t true; following the rules isn’t enough. Hackers continually hone their skills and develop their tools. Penetration testing is vital to keep up with them.
How Organizations Can Maximize Pentesting Results
Before the test, it’s important to define the scope of the test. What systems, applications, and cloud environments do you want to test? At this point, it’s important to get executive buy-in and avoid common pitfalls, such as overlooking third-party integrations. Poor scoping can lead to critical systems being excluded from testing, giving a false sense of security.
After the test, it’s critical to review findings and take concrete action to remediate them. Sometimes organizations simply report the findings without implementing a policy or action to fix the issues. Last, it’s critical to re-test to verify that the fixes worked. Skipping re-testing is one of the most common mistakes. Without verification, it’s impossible to confirm that an organization has successfully resolved the vulnerabilities.
Choosing the Right Pentesting Provider: Internal vs. External
It’s important to look for a mature team with the right credentials, certifications, and experience, especially experience with building the systems the test will attack. Certifications such as OSCP or CEH validate technical skill, while clear, business-relevant reporting ensures stakeholders at all levels can act on findings. An organization’s track record and its willingness to demonstrate testing methodology are also important factors.
Key Takeaways
Here are the top lessons organizations should keep in mind when approaching penetration testing:
- Penetration testing actively challenges your security, not just scans for issues.
- It goes beyond compliance to identify true risk exposure.
- Effective testing requires clear scoping, skilled testers, and follow-through on remediation.
- Re-testing confirms issues are resolved and helps maintain security posture.
