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Pentesting Active Directory and Windows-based Infrastructure

Pentesting Active Directory and Windows-based Infrastructure

By : Denis Isakov
4.9 (14)
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Pentesting Active Directory and Windows-based Infrastructure

Pentesting Active Directory and Windows-based Infrastructure

4.9 (14)
By: Denis Isakov

Overview of this book

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.
Table of Contents (13 chapters)
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Abusing Active Directory Certificate Services

In the next two chapters, we will cover services that can be found in almost every environment but are not installed by default during Active Directory deployment. We will start with Active Directory Certificate Service (AD CS). This service is Microsoft’s implementation of a Public Key Infrastructure (PKI) integrated with Active Directory. It allows us to utilize public key cryptography throughout the Active Directory forest, providing certificates, digital signatures, code signing, and other capabilities. As usual, with great power comes great responsibility. AD CS has been often overlooked in terms of hardening and monitoring due to its complex nature. In June 2021, SpecterOps released a comprehensive research paper where they described known and new ways to attack AD CS[1].

We will start our learning journey by explaining the necessary PKI theory. We will then cover possible ways to steal certificates and achieve persistence...

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