Penetration Tests: Useful, Pointless, Harmful, Required, Ineffective? - Phillip Wylie, Marina Segal - ESW #398

Penetration tests are a ubiquitous part of modern cybersecurity consulting services. Every business above a certain size has likely hired an external firm to conduct a pentest at some point in the past. But have you ever stopped to think about whether these tests are truly effective? In this episode of Enterprise Security Weekly, we'll be discussing the effectiveness of penetration tests and what's going wrong.

According to Phillip Wylie, one of the experts being interviewed on this episode, many penetration tests look an awful lot like standard ransomware attacks. This raises a crucial question: if our pentests are so similar to real-life attacks, why do we keep falling victim to them?

The issue is not with the pentesters themselves, but rather with the organizations they're testing. The reality is that thousands of companies every year fall victim to ransomware attacks, despite having conducted penetration tests in recent years.

Marina Segal, founder and CEO of Tamnoon, joins us to shed some light on this issue. Her company was founded specifically to address these problems, including the cybersecurity skills gap and the growing importance of cloud security. According to Gartner, by 2025, 75% of new Cloud Security Posture Management (CSPM) purchases will be part of an integrated Cloud Native Application Protection Platform (CNAPP) offering.

This highlights the growing importance of CNAPP solutions, which combine advanced tools and technologies to address cloud security challenges. However, even well-intentioned teams may inadvertently leave their systems vulnerable due to the cybersecurity skills shortage, according to experts like Marina Segal.

Another issue is the gap in addressing Kubernetes-specific security issues. CSPMs and CNAPPs may have limitations when it comes to tackling these unique security challenges.

So what can be done? According to Marina Segal, investing in training to bridge the cybersecurity skills gap and leveraging CNAPP platforms that combine advanced tools are recommended strategies for organizations looking to improve their cloud security posture.

The State of Remediation 2025 Report

In this week's enterprise security news, we have a new report from Tamnoon that highlights the growing importance of addressing remediation challenges in cloud security. By 2034, the CNAPP market is expected to grow from $10.74 billion to $59.88 billion, indicating a significant increase in demand for these solutions.

Enterprise Security Weekly

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Conclusion

Penetration tests are an essential part of modern cybersecurity consulting services. However, if they're not conducted effectively and with the right mindset, they may not be providing the level of protection that organizations need.

In conclusion, we hope you've gained a better understanding of the importance of cloud security and the challenges that come with it. By investing in training and leveraging CNAPP platforms, organizations can improve their cloud security posture and stay ahead of emerging threats.