CypherCon 2025

Optimal Offensive Security Programs

Phillip Wylie

Abstract:

Offensive security is a critical component of cybersecurity, as it involves identifying and exploiting system vulnerabilities from a threat actor’s perspective. This approach to security assessments can reveal vulnerabilities that may not be detected through vulnerability scanning alone. However, offensive security can be complex and is often misunderstood, which can hinder organizations from achieving their security assessment objectives. Additionally, current offensive security assessment practices often contain gaps that reduce the effectiveness of these assessments. In this presentation, experienced offensive security professional and educator Phillip Wylie will explore the various types of assessments that constitute offensive security, examine common gaps encountered during pentests, and offer strategies to enhance offensive security efforts. This session aims to provide attendees with a better understanding of offensive security, insight into different offensive security assessment types, guidance on addressing common gaps associated with offensive security, and information on how it integrates with vulnerability management programs.

Phillip Wylie

Dr. Pepper!

Phillip Wylie is a cybersecurity professional with over 27 years of industry experience in IT and cybersecurity. He is also a former Dallas College Adjunct Instructor and the founder of The Pwn School Project and DEFCON Group 940. Phillip has diverse experience in multiple cybersecurity disciplines, including network security, application security, and pentesting. As an offensive security professional with over a decade of experience, he has conducted pentests of networks, Wi-Fi networks, applications, red team operations, and social engineering.

Phillip’s contributions to the cybersecurity industry extend beyond his work as a pentester. He is the concept creator and co-author of “The Pentester BluePrint: Starting a Career as an Ethical Hacker,” a highly regarded book inspired by a lecture he presented to his class at Dallas College, which later became a conference talk. Phillip hosts “The Phillip Wylie Show” and “The Hacker Factory Podcast,” where he interviews guests on how they got started in cybersecurity and their advice for aspiring cybersecurity professionals. Additionally, he is a frequent conference speaker, workshop instructor, and mentor.