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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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Forced authentication

We have covered MITM capabilities and now will discuss in detail various ways to force authentication. The idea is that a standard user can force the target machine account (usually a domain controller) to connect to an arbitrary target. This is made possible through an automatic authentication attempt. You can find a repository with 15 known methods in 5 protocols[10]. Now, let’s dive a bit deeper into each method.

MS-RPRN abuse (PrinterBug)

This is a won’t-fix bug, which is enabled by default in every Windows environment. The idea is that by using a domain username and password, the attacker can trigger the RpcRemoteFindFirstPrinterChangeNotificationEx method and force authentication over SMB. We will demonstrate this attack later when discussing Kerberos’s unconstrained delegation in Chapter 5. A go-to tool for this abuse is called SpoolSample[11] and can be found on GitHub.

MS-EFSR abuse (PetitPotam)

The Encrypting File System...

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