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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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Roasting the three-headed dog

It was inevitable that we would reach a point where we must discuss and understand Kerberos. This authentication protocol was built to access services in the network by presenting a valid ticket.

Kerberos 101

We need a bit more of an understanding of how the protocol works before we can discuss the attack venues available for us. As a good starting point, I can recommend the blog post by hackndo[17]

We have three main subjects – the client, service, and Key Distribution Center (KDC), which is the domain controller. The following diagram[18], which was published on the Microsoft website, explains how it works:

Figure 4.8 – Kerberos in a nutshell

Now let follow the authentication process in more details step-by-step.

  1. KRB_AS_REQ (Kerberos Authentication Service Request) is sent by the client to KDC and contains various information, most importantly, a timestamp that is encrypted with the hashed...

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