Pentesting Active Directory and Windows-based Infrastructure

Enhance your skill set to pentest against real-world Microsoft infrastructure with hands-on exercises and by following attack/detect guidelines with OpSec considerations

Key Features

• Find out how to attack real-life Microsoft infrastructure
• Discover how to detect adversary activities and remediate your environment
• Apply the knowledge you’ve gained by working on hands-on exercises
• Purchase of the print or Kindle book includes a free PDF eBook

Book Description

This book teaches you the tactics and techniques used to attack a Windows-based environment, along with showing you how to detect malicious activities and remediate misconfigurations and vulnerabilities.

You’ll begin by deploying your lab, where every technique can be replicated. The chapters help you master every step of the attack kill chain and put new knowledge into practice. You’ll discover how to evade defense of common built-in security mechanisms, such as AMSI, AppLocker, and Sysmon; perform reconnaissance and discovery activities in the domain environment by using common protocols and tools; and harvest domain-wide credentials. You’ll also learn how to move laterally by blending into the environment’s traffic to stay under radar, escalate privileges inside the domain and across the forest, and achieve persistence at the domain level and on the domain controller. Every chapter discusses OpSec considerations for each technique, and you’ll apply this kill chain to perform the security assessment of other Microsoft products and services, such as Exchange, SQL Server, and SCCM.

By the end of this book, you’ll be able to perform a full-fledged security assessment of the Microsoft environment, detect malicious activity in your network, and guide IT engineers on remediation steps to improve the security posture of the company.

What you will learn

• Understand and adopt the Microsoft infrastructure kill chain methodology
• Attack Windows services, such as Active Directory, Exchange, WSUS, SCCM, AD CS, and SQL Server
• Disappear from the defender’s eyesight by tampering with defensive capabilities
• Upskill yourself in offensive OpSec to stay under the radar
• Find out how to detect adversary activities in your Windows environment
• Get to grips with the steps needed to remediate misconfigurations
• Prepare yourself for real-life scenarios by getting hands-on experience with exercises

Who this book is for

This book is for pentesters and red teamers, security and IT engineers, as well as blue teamers and incident responders interested in Windows infrastructure security. The book is packed with practical examples, tooling, and attack-defense guidelines to help you assess and improve the security of your real-life environments. To get the most out of this book, you should have basic knowledge of Windows services and Active Directory.

Table of Contents

1. Getting the Lab Ready and Attacking Exchange Server
2. Defense Evasion
3. Domain Reconnaissance and Discovery
4. Credential Access in Domain
5. Lateral Movement in Domain and Across Forests
6. Domain Privilege Escalation
7. Persistence on Domain Level
8. Abusing Active Directory Certificate Services
9. Compromising Microsoft SQL Server
10. Taking over WSUS and SCCM