Penetration Tests: useful, pointless, harmful, required, ineffective? - Phillip Wylie - ESW #398

Penetration Tests: useful, pointless, harmful, required, ineffective? - Phillip Wylie - ESW #398

Author: Security Weekly Productions March 17, 2025 Duration: 32:12

Penetration tests are probably the most common and recognized cybersecurity consulting services. Nearly every business above a certain size has had at least one pentest by an external firm.

Here's the thing, though - the average ransomware attack looks an awful lot like the bog standard pentest we've all been purchasing or delivering for years. Yet thousands of orgs every year fall victim to these attacks. What's going on here? Why are we so bad at stopping the very thing we've been training against for so long?

This Interview with Phillip Wylie will provide some insight into this! Spoiler: a lot of the issues we had 10, even 15 years ago remain today.

Segment resources:

Show Notes: https://securityweekly.com/esw-398


Hosted by Adrian Sanabria, Enterprise Security Weekly (Video) is a deep dive into the complex world of protecting large organizations. This isn't just a headline recap; it's a practical, analyst-level discussion for security professionals who need to understand the "why" behind the news. Each episode from Security Weekly Productions brings together a seasoned panel including co-hosts like Katie Teitler-Santullo, Ayman Elsawah, Jason Wood, Jackie McGuire, and Sean Metcalf to dissect emerging threats, architectural shifts, and the tools that promise to help. You'll hear candid evaluations as they put security vendors and their claims under the microscope, separating hype from genuine utility. The conversation revolves around actionable intelligence and strategic trends that empower defenders to build more resilient environments. Tuning into this podcast provides a consistent, informed perspective that cuts through the noise of the daily alert cycle, offering clarity and context that's often hard to find. It’s a video format that adds a layer of connection and detail to these technical discussions, making complex topics more accessible. If your work involves making critical decisions about enterprise security posture, this series serves as a vital resource for staying informed and ahead of the curve.
Author: Language: English Episodes: 100

Enterprise Security Weekly (Video)
Podcast Episodes