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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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Domain persistence

In this section, we will explore techniques to achieve persistence in the domain using a compromised CA. We will gain an understanding of the typical vectors an adversary will utilize to keep high-privileged access to the environment and explore approaches to detect such activities.

DPERSIST1 – Forge certificates with stolen CA certificate

If an adversary has compromised a CA and obtained a CA certificate with a corresponding private key, it is possible to forge any certificate in the domain environment. To differentiate the CA certificate from others, pay attention to certain characteristics such as the following:

  • The issuer and subject are set to the distinguished name of the CA
  • It has a “CA Version” extension
  • No EKU

These characteristics are shown in the following screenshot:

Figure 8.44 – CA certificate information

Figure 8.44 – CA certificate information

It is important to mention that forged certificates cannot...

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