Redefining Hacking: A Comprehensive Guide to Red Teaming and Bug Bounty Hunting in an AI-driven World

by Omar Santos, Savannah Lazzara, Wesley Thurner

Overview

Redefining Hacking: A Comprehensive Guide to Red Teaming and Bug Bounty Hunting in an AI-Driven World equips cybersecurity professionals, students, and tech enthusiasts with modern hacking methodologies and the tools to combat evolving threats. Written by industry experts Omar Santos, Savannah Lazzara, and Wesley Thurner, this book blends real-world insights with forward-looking perspectives on AI, automation, and quantum computing. Packed with hands-on exercises, actionable strategies, and case studies, it empowers readers to think like attackers while proactively strengthening their defenses. Gain practical knowledge to master red teaming, bug bounty hunting, and prepare for an AI-influenced cybersecurity landscape.

This practical forward-thinking book provides: 

• Holistic Coverage: Comprehensive insights into red teaming and bug bounty hunting
• Future Trends: Explore AI, automation, and quantum computing’s impact on security
• Hands-On Learning: Includes exercises, review questions, and GitHub resources
• Expert Guidance: Authored by seasoned cybersecurity professionals with diverse expertise

Product Details

ISBN-13:	9780138363574
Publisher:	Pearson Education
Publication date:	03/14/2025
Sold by:	Barnes & Noble
Format:	eBook
File size:	58 MB
Note:	This product may take a few minutes to download.
Age Range:	18 Years

About the Author

Omar Santos is a Distinguished Engineer at Cisco who pioneers advancements in artificial intelligence security, cybersecurity research, ethical hacking, incident response, and vulnerability disclosure. As co-chair of the Coalition for Secure AI (CoSAI) and board member of the OASIS Open standards organization, he shapes the future of secure technology adoption across industries.

Omar drives innovation through multiple leadership roles, including as founder of OpenEoX and co-chair of the Forum of Incident Response and Security Teams (FIRST) PSIRT Special Interest Group. His commitment to cybersecurity education and community building is evident in his role as the co-founder and one of the leaders of the DEF CON Red Team Village and the chair of the Common Security Advisory Framework (CSAF) technical committee.

Omar has published over 20 books, created over 20 video courses, and contributed more than 40 academic research papers to the field. Omar's work in cybersecurity is also recognized through multiple granted patents. You can follow Omar in X at https://x.com/santosomar and LinkedIn at https://www.linkedin.com/in/santosomar.

Savannah Lazzara is a Security Engineer specializing in red teaming at a tech company. Savannah has multiple years of experience in security consulting working with many Fortune 500 corporations and      has experience in carrying out security assessments, which include network assessments, social engineering exercises, physical facility penetration tests, and wireless assessments. Savannah also has experience in performing adversary simulation assessments, which include remote red team simulations, insider threat assessments, and onsite red team assessments. Savannah’s area of expertise is focused on social engineering and physical security.

Savannah is the co-lead of Red Team Village. Additionally, Savannah has spoken at various cybersecurity conferences, including Source Zero Con, BSides, and others. Savannah has also spoken on multiple podcast shows including The Hacker Factor and Hackerz and Haecksen.

Wesley Thurner is a Principal Security Engineer on the Intuit Red Team, designing and leading transformative security initiatives across the organization. He accomplishes this through multiple internal roles. Wesley leaders the internal Purple Team, is an Ambassador for cybersecurity education throughout the workforce and leads working groups to define security policies.

Prior to Intuit, Wesley served as an exploitation operator in the U.S. Department of Defense's most elite computer network exploitation (CNE) unit. There he led and developed multiple teams across a variety of roles in the U.S. Air Force's premier selectively manned cyberattack squadron. Wesley is also a co-lead for the Red Team Village, a community-driven village bridging the gap between penetration testers and offensive operations. He has spoken at various cybersecurity conferences and authored numerous training courses as well as white papers.

Table of Contents

Chapter 1:The Evolution of Penetration Testing, Red Teaming, and Bug Bounties.. . . . . . . 1

    Into the Abyss.. . . . . . . 1

    Industry Overview. . . . . . . 5

    The Early Days and Evolution of Penetration Testing.. . . 7

    The Rise of Red Teaming. . . . . . 9

    The Emergence of Bug Bounty Programs.. . . . 10

    The Convergence of Penetration Testing, Red Teaming, and Bug Bounties.. 11

    The Future of Penetration Testing, Red Teaming, and Bug Bounties. . 12

    The Increasing Use of AI and ML in Penetration Testing,

    Red Teaming, and Bug Bounties.. . . . . 13

    Test Your Skills. . . . . . . 15

Chapter 2 Introduction to Red Teaming.. . . . . 17

    What Is Red Teaming?. . . . . . 17

    The Importance of Red Teaming. . . . . 18

    Red Team Frameworks and Methodologies.. . . . 20

    Red Team Engagements.. . . . . . 22

    Red Team Challenges.. . . . . . 26

    References. . . . . . . 28

    Test Your Skills. . . . . . . 30

Chapter 3 Red Team Infrastructure.. . . . . . 33

    An Overview of Red Team Infrastructure.. . . . 34

    Command and Control.. . . . . . 34

    Test Your Skills. . . . . . . 60

Chapter 4 Modern Red Team Methodology and Tools.. . . . 63

    Planning.. . . . . . . 64

    Reconnaissance. . . . . . . 65

    Initial Access.. . . . . . . 81

    Persistence.. . . . . . . 96

    Lateral Movement. . . . . . . 97

    Post-Exploitation. . . . . . . 105

    Reporting.. . . . . . . 105

    Test Your Skills. . . . . . . 107

Chapter 5 Social Engineering and Physical Assessments. . . 109

    Phone Pretexting: Let’s Dial into Your Target. . . . 110

    Spear Phishing: Time to Reel In Your Target.. . . . 115

    Infrastructure.. . . . . . . 116

    Formulating Your Email or Instant Message. . . . 128

    Execution.. . . . . . . 130

    Can You Hear Us from the Inside?. . . . . 131

    Test Your Skills. . . . . . . 144

Chapter 6 Advanced Post-Exploitation Techniques.. . . . 147

    An Overview of Post-Exploitation. . . . . 148

    How to Maintain Access, Use Persistence Mechanisms, and

    Create Backdoors.. . . . . . 152

    Command and Control (C2) and Covert Channels.. . . 180

    How to Perform Lateral Movement. . . . . 186

    Legitimate Utilities and Living Off the Land.. . . . 189

    Post-Exploitation Privilege Escalation. . . . . 197

    Test Your Skills. . . . . . . 202

Chapter 7 Active Directory and Linux Environments.. . . . 207

    Active Directory Fundamentals. . . . . 208

    Microsoft Entra ID and Azure.. . . . . 223

    Active Directory Attack Techniques. . . . . 229

    Advanced Linux Environment Attack Techniques. . . 267

    Test Your Skills. . . . . . . 277

Chapter 8 The Future of Red Teaming Beyond the AI Revolution.. . 281

    Understanding the Current State of AI in Red Teaming.. . . 282

    Creating AI-Powered Offensive Security Tools.. . . . 283

    Examining Fine-Tuned Uncensored AI Models.. . . . 297

    Understanding Retrieval-Augmented Generation (RAG) for Red Teaming.. 299

    Red Teaming AI and Autonomous Systems. . . . 313

    Keeping Pace with Rapidly Evolving Technologies. . . 322

    Test Your Skills. . . . . . . 324

Chapter 9 Introduction to Bug Bounty and Effective Reconnaissance. . 327

    Understanding Bug Bounty Programs.. . . . 328

    Exploring Effective Reconnaisance.. . . . . 336

    Performing Active Reconnaissance. . . . . 377

    Understanding the Art of Performing Vulnerability Scans.. . . 396

    Performing Web Application and API Recon. . . . 401

    Communicating Your Findings and Creating Effective

    Bug Bounty Reports.. . . . . . 407

    Test Your Skills. . . . . . . 410

    Exercises.. . . . . . . 412

Chapter 10 Hacking Modern Web Applications and APIs. . . . 415

    Overview of Web Application-Based Attacks, the OWASP

    Top 10 for Web Applications, and OWASP Top 10 for LLM Applications. 416

    Building Your Own Web Application Lab.. . . . 429

    Understanding Business Logic Flaws.. . . . . 430

    Understanding Injection-Based Vulnerabilities. . . . 432

    Exploiting Authentication-Based Vulnerabilities. . . . 451

    Exploiting Authorization-Based Vulnerabilities. . . . 461

    Understanding Cross-Site Scripting (XSS) Vulnerabilities.. . . 463

    Understanding Cross-Site Request Forgery and Server-Side

    Request Forgery Attacks.. . . . . . 472

    Understanding Clickjacking.. . . . . 480

    Exploiting Security Misconfigurations. . . . . 480

    Exploiting File Inclusion Vulnerabilities. . . . 482

    Exploiting Insecure Code Practices. . . . . 484

    Using Additional Web Application Hacking Tools. . . 488

    Test Your Skills. . . . . . . 493

Chapter 11 Automating a Bug Hunt and Leveraging the Power of AI.. . 497

    Traditional Bug Hunting Methods. . . . . 498

    AI-Powered Automation in Bug Hunting.. . . . 500

    AI Model Training, Fine-Tuning, and RAG for Bug Bounties. . . 516

    Challenges of Using AI for Bug Bounty Hunting. . . . 521

    Test Your Skills. . . . . . . 523

Appendix Answers to Multiple-Choice Questions.. . . . . 527

 

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