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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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Relaying the hash

In the previous chapter, we covered different possibilities to capture the NTLM response by forcing authentication or using MitM. Now we are getting to the answer of why we want to capture responses. Before we jump into practice, some theory concepts and caveats need to be explained first.

First, there are two versions of the NTLM protocol (v1 and v2). Next, NTLM authentication messages can be relayed cross-protocol as they are protocol-independent. It is important to understand what protocol was used to capture NTLM authentication and what protocol we are planning to relay it over. The following mindmap was created by nwodtuhs and is a good reference for our discussion.

Figure 5.6 – NTLM relay

Figure 5.6 – NTLM relay

Let us focus more on an important topic, which is signing, especially for SMB and LDAP. Signing configuration and existence is controlled by settings on the client and server side. For SMB, it will depend on the protocol version and whether...

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