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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 privilege escalation

In this section, we will explore practical techniques to escalate privileges by exploiting various security issues, such as template and extension misconfigurations (ESC1, 2, 3, 9, and 10), improper access controls (ESC4, 5, and 7), CA misconfiguration (ESC6), and relay attacks (ESC8 and 11). I have chosen such a grouping of the attacks from[12]. But to begin with, we will start with a critical vulnerability discovered by Oliver Lyak, called Certifried, which evolves into ESC9 and ESC10 after the patch.

Certifried (CVE-2022-26923)

This vulnerability has much in common with samAccountName spoofing (CVE-2021-42278). Original research by the author is published here[13].

In AD CS, by default, there are two authentication certificates: user and machine. Every user account has a User Principal Name (UPN) that must be unique. The UPN is embedded into the certificate and used by KDC during authentication. Computer accounts do not have a UPN, as dNSHostName...

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