Traditional vs Generative AI Pentesting: A Hands-On Approach to Hacking

Cover....1

Half Title....2

Title Page....4

Copyright Page....5

Dedication....6

Table of Contents....8

Preface....9

About the author....11

Chapter 1: Foundations of pentesting: Methodologies, frameworks, and AI integration....12

Introduction....12

What is PT?....13

Benefits of conducting a PT....13

Comparison of security audit vulnerability assessment and PT....14

Pentesting vs ethical hacking....15

Pentesting benefits....15

PT strategies....16

Black-box penetration testing....16

White-box penetration testing....17

Gray-box penetration testing....17

Pentesting vs red teaming....17

Common areas of penetration testing....18

PT process....19

Code of good practice....19

Legal framework: Rules of Engagement (RoE)....20

Legal framework: Non-disclosure agreement (NDA)....21

Understanding the restrictions....21

Characteristics of a good PT....23

When should a PT be conducted?....23

Pentester ethics....23

PT methodologies....23

OSSTMM methodology....23

Phase I: Regulatory....24

Phase II: Definitions....24

Phase III: Information phase....24

Phase IV: Interactive control test phase....24

Advantages....24

Limits....24

PTES methodology....25

The stages of the PTES methodology....25

Pre-commitment interactions....25

Information gathering....25

Threat modeling....25

Vulnerability analysis....25

Operation....25

Post-op....26

Reports....26

Benefits....27

Limits....27

NIST methodology SP 800-115....27

The ISSAF (Information Systems Security Assessment Framework)....27

OWASP methodology....28

The OWASP phases....29

Benefits of OWASP....29

Limits of OWASP....29

Cyber kill chain methodology....30

MITRE ATT&CK....31

Adversary profile....33

Contribution of MITRE....33

Tools for pentesting according to MITRE ATT&CK....33

Challenges in penetration testing....37

AI-driven penetration testing....38

Key features of AI-driven penetration testing....39

Benefits of AI-driven penetration testing....39

Tools for AI-driven penetration testing....39

Challenges and ethical considerations....40

Overreliance on AI....40

Ethical and legal concerns....41

Inherent bias in AI models....41

Skill gap in using AI tools....41

Risks associated with generative AI in penetration testing....41

Escalation of cyber threats....41

Advanced persistent threats (APTs)....42

Autonomous and self-propagating attacks....42

Uncontrolled AI development....42

Conclusion....42

References....42

Chapter 2: Building a modern penetration testing lab with generative AI....45

Technical requirements....45

Set up a virtual PT laboratory....45

Your security....45

Understanding virtualization technology....46

Target machines....47

Metasploitable 2....47

Step 1: Download and install VirtualBox on your PC....47

Step 2: Install Kali Linux on VirtualBox....47

Kali Linux basic commands....51

PT tools....52

PT platform....52

Information gathering....52

Vulnerability scanner Nessus and Openvas....54

Web application testing platforms....54

Examples of training platforms....54

Generative AI in penetration testing....55

Conclusion....60

References....60

Chapter 3: GenAI-driven reconnaissance for effective penetration testing....61

Reconnaissance....61

Objectives of reconnaissance and footprinting....61

Types of footprinting....61

Passive footprinting....61

Methods of Passive Footprinting:....61

Active footprinting....62

Methods of active footprinting....62

Importance of reconnaissance....62

Types of information collected during footprinting....62

Organizational information....62

Network information....63

System information....63

Footprinting methodology....63

Key sources for information gathering....63

Methodological approach....64

Footprinting through search engines....64

Information extracted through search engines....64

Applications in footprinting....66

Google....66

Example of using google operators....66

Metasearch engines....69

Footprinting using advanced Google hacking techniques with AI....70

Example of AI-powered Google hacking....70

Advanced Google hacking with shell command....71

VPN footprinting through Google hacking....72

Automating VPN footprinting with AI....72

NetCraft: Website search engine....74

Social media....75

Example: LinkedIn....75

Example: Facebook....78

OSINT automation tools....79

Finding the target’s domain and subdomains....79

Fingerprinting the target using Shodan....82

Recon-ng: An OSINT tool Web....84

TheHarvester....84

Metagoofil (http://www.edge-security.com)....88

SpiderFoot: An OSINT tool recognition....90

OSINT framework....93

Maltego: A framework for collecting information....96

OSINT with DNS querying....98

Perform Whois lookups....98

APNIC Whois lookup (source: https://www.oonic.net)....99

ARIN WhOIS.RIS (source: http://whois.arin.net)....100

Dnsenum (https://github.com)....100

Nslookup (source: https://docs.microsoft.com)....101

What does a non-authoritative answer mean?....101

Lookup DNS records for the domain....103

Reverse domain name search....104

Find a website’s domain name from its IP address....104

Finding a company’s Top-Level Domains (TLDs) and subdomains with AI....104

Example 1: Enumerate subdomains with Sublist3r....104

Reverse DNS Lookup....106

Performing DNS enumeration with DNSRecon....106

DNSdumpster....108

Draw a network diagram using traceroute analysis....109

Traceroute....109

Example of AI-enhanced tracerouting....109

AI-powered OSINT tools....110

Key use cases of AI in OSINT....110

Benefits of AI in OSINT....111

Notable AI-powered OSINT tools....111

Footprinting using AI script....111

Automating domain footprinting with AI....111

Documentation of result....112

Conclusion....112

References....113

Chapter 4: GenAI-enhanced scanning and sniffing....114

Introduction....114

Nmap: Network mapper....115

Installation of Nmap....116

Installing on Linux....116

Installation on Windows....116

Install on macOS....116

Using Nmap....117

Basic syntax....117

Examples of use....117

Scan options....117

Output options....118

Identification options....118

Port options....118

Attack options....118

Examples of advanced use....118

Nmap: TCP Connect Scan sT....118

Nmap: TCP SYN Scan sS (Stealth)....119

Nmap: UDP Scan sU....120

Nmap: The scripts....120

NMAP: Examples....120

NMAP Scanning with AI....121

Example #1....121

Example #2....121

Example #3....121

Example #4....123

Firewall Evasion....123

Example....123

Nmap to fragment....124

Example....124

Script to automate network scanning tasks with AI....125

Hping3....125

Key features....126

Advanced applications....126

Syntax....126

Hping commands....128

Hping Scan with AI....128

Example 2....129

Metasploit....130

Network sniffing....131

How a sniffer works....131

Types of sniffing....132

Sniffing passive....132

Sniffing active....132

Protocols vulnerable to sniffing....133

Get Wireshark....134

Demer's Wireshark....134

Packet color coding....137

Packet filtering in Wireshark....137

Attack and defend with Wireshark....139

How do you catch a network scan attack?....139

How do I detect running local services (accessible to the web)?....139

Creating firewall rules....141

Packet capture....141

HTTP traffic....141

Traffic FTP....145

Traffic HTTPS....146

Conclusion....153

References....153

Chapter 5: Vulnerability assessment: Tools, techniques, and GenAI integration....155

Introduction....155

Background....156

Vulnerability....156

Vulnerability classification....156

Vulnerability research....157

What is vulnerability assessment?....158

Characteristics of a good vulnerability assessment solution....158

Vulnerability assessment systems and databases....159

Types of scanners....159

General-purpose scanners....159

Web application scanners....159

Specific application scanners....159

Scanner types by authentication....160

Unauthenticated scanners....160

Authenticated scanners....160

Agent-based scanners....160

Resources for vulnerability research....160

Vulnerability assessment tools....160

Nessus....160

Installation....161

Scan console....162

Start a scan....162

Run a basic scan....163

Run a web scan....164

Web Scan Results (Figure 5.9)....166

Rapid7 Nexpo....167

Running Vulnerability Scanning....167

OpenVAS....170

Nikto (Source: https://cirt.net)....175

Characteristics....177

OWASP Zap (https://www.zaproxy.org)....177

Automated scanning....177

Alerts....177

Generate a report....180

Scan web servers and applications for vulnerabilities using Nikto....181

Scan wordpress sites with WPscan....183

Wordpress scan through AI....185

Vulnerability assessment using AI....186

Example usage....186

Explanation....187

Explanation....187

Vulnerability scanning using Nmap with AI....187

Command example....188

Vulnerability assessment using Python script and AI....188

Concept and approach....188

Skipfish vulnerability scanning with AI....189

Database vulnerability assessment....189

Vulnerability assessment reports....191

Structure of vulnerability assessment reports....191

Components of a vulnerability assessment report....191

Classification of reports....192

Conclusion....192

References....192

Chapter 6: AI-driven social engineering and penetration testing....194

Introduction....194

Social engineering concepts....195

PT by social engineering: An overview....195

Black box or white box test?....196

Types of social engineering....196

Human-based social engineering....196

Computer-based social engineering....196

Example of social engineering by e-mail....197

Mobile-based social engineering....197

Methods of influence....201

The importance of phishing campaigns....201

Phishing tools....201

Launch a phishing campaign....202

Social engineering using different techniques....202

The social engineering toolkit....202

Using setoolkit for attacks phishing....202

Socialphish phishing....205

Installation....207

Uses....208

Detecting a phishing attack....210

Objectives of the Lab....210

Detecting phishing with Netcraft....210

Detecting phishing with PhishTank....213

Audit organization’s security for phishing attacks....214

Gophish (​https://​getgophish.​com)....218

Creating phishing emails with ChatGPT....226

Handwriting style for identity theft....226

Writing style for identity theft (example)....227

Identity theft using AI: Creation of Deepfake videos....228

Purpose of Deepfakes....229

Technologies and tools used....229

Conclusion....230

References....230

Chapter 7: GenAI-driven exploitation testing techniques....231

Technical requirements....231

Why consider exploiting a target machine during a test?....231

Reverse vs bind shell....232

Staged vs non-staged payloads....234

Exploiting vulnerabilities: Categories of exploits....234

Exploiting vulnerabilities....234

Metasploit....235

Useful Metasploit user interfaces....236

Metasploit modules....236

Meterpreter....237

Basic commands in Meterpreter....237

Process commands....238

File System Commands....238

Networking Commands....238

User Interface Functionalities....238

Feat-db: searchsploit....238

Find modules....240

Feat-DB....240

Rapid7 exploits database....240

0day.today....242

Preparing the Metasploit environment....242

Identifying the target of the attack....242

Identify the target’s vulnerabilities....242

Vsftpd Backdoor v2.3.4....242

Launch attacks using the Metasploit framework....242

Exploit FTP Backdoor through GenAI....247

Exploit with the UnreaIRCD IRC backdoor....247

Metasploit options, shells, and payloads....249

Feat SMB on Windows via EternalBlue....250

Finding a vulnerable target....251

Find a module to use....251

Shells....252

Verify that the target is compromised....253

Lab: Penetration testing with Metasploit....253

Exploit Steps....254

Payload and exploit generation....264

Perform system hacking using ShellGPT....264

Generate a payload....265

Conclusion....266

References....267

Chapter 8: Post-exploitation techniques and AI-driven privilege escalation....268

Introduction....268

Post-exploitation techniques....268

File transfer techniques: Push vs pull....269

File transfer services....269

Alternative methods for file transfer....270

Alternative file transfer methods....270

Looting files....271

File transfer....271

Evasion tactics....271

Pivoting and cracking....272

The primacy of passwords....272

Password guessing vs. password cracking....272

Synchronized passwords....273

Dictionaries for password cracking....273

Improving speed in password cracking....273

Passwords without cracking....274

Attention to information leaks....274

Best practices for handling passwords....274

Post-test analysis and reporting....275

Dumping hashes with Meterpreter....275

Dumping credentials with Mimikatz....275

Why pivot?....276

Pivoting using metasploit’s route command....276

SSH local port forwarding....276

SSH remote port forwarding....276

SSH dynamic port forwarding....277

Port forwarding via a Meterpreter session....277

Meterpreter sessions via MSF route....277

SSH local and dynamic port forwarding....278

Cracking passwords with John the ripper....279

Multithreaded and GPU cracking with Hashcat....279

Elevation of privilege....279

Elevation of privilege: The enumeration....280

User enumeration....280

Elevation of privilege: The enumeration....281

Host name enumeration....283

Enumerating the OS version and architecture....284

Automating enumeration with GENAI tools....285

Exploit kernel vulnerabilities through AI....287

Identify the kernel version....287

Elevation of privilege: sudo....288

Elevation of privilege: SUID/GUID....289

Search and use of SUID files....289

SUID....289

Example of SUID operation....289

Lateral movements....290

Example 1....290

Persistence....291

Backdoor....291

Example 2: Creating a backdoor with msfvenom....292

Example 3: Sticky keys persistence....292

Example 4: Automating the process with a script....292

Privilege escalation to collect the Hashdump using Mimikatz....293

Conclusion....302

References....302

Chapter 9: GenAI for automating and enhancing penetration testing reports....303

Introduction....303

Risk ranking....304

General findings....305

Strategic roadmap....305

Technical report....306

Tools used....306

Information gathering....306

Vulnerability assessment and exploitation....306

Post-op....307

Conclusion....308

Appendices....308

Use Case: Automating PT reports with generative AI and Dradis....308

Pentest findings....308

Evaluation of findings....309

Report-writing through GenIA tools....309

Executive summary....309

Test methodology....310

Detailed findings....310

Recommendations....311

Conclusion....311

Submission of PT report....311

Report retention....312

Closing document....312

Conclusion....312

References....312

Index....314

Traditional vs Generative AI Pentesting: A Hands-On Approach to Hacking explores the evolving landscape of penetration testing, comparing traditional methodologies with the revolutionary impact of Generative AI. This book provides a deep dive into modern hacking techniques, demonstrating how AI-driven tools can enhance reconnaissance, exploitation, and reporting in cybersecurity assessments.

Bridging the gap between manual pentesting and AI automation, this book equips readers with the skills and knowledge to leverage Generative AI for more efficient, adaptive, and intelligent security testing. By blending practical case studies, hands-on exercises, and theoretical insights, it guides cybersecurity professionals, researchers, and students through the next generation of offensive security strategies.

The book offers comprehensive coverage of key topics, including:

• Traditional vs AI-Driven Pentesting: Understanding the evolution of security testing methodologies
• Building an AI-Powered Pentesting Lab: Leveraging Generative AI tools for reconnaissance and exploitation
• GenAI in Social Engineering and Attack Automation: Exploring AI-assisted phishing, deepfake attacks, and deception tactics
• Post-Exploitation and Privilege Escalation with AI: Enhancing persistence and lateral movement techniques
• Automating Penetration Testing Reports: Utilizing AI for streamlined documentation and risk analysis

This book is an essential resource for ethical hackers, cybersecurity professionals, and academics seeking to explore the transformative role of Generative AI in penetration testing. It provides practical guidance, in-depth analysis, and cutting-edge techniques for mastering AI-driven offensive security.