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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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Lab architecture and deployment

Even if creating and deploying a test lab can be daunting and time consuming, it is an important preparation step before jumping into attack emulation. MITRE ATT&CK has a dedicated tactic for this activity called Resource Development.

There are a few free but formidable projects available for automated lab deployment. You can choose any of them depending on your workstation’s resources and replicate the vulnerabilities yourself. For example, there is a very good open source project maintained by the Splunk Threat Research Team called Splunk Attack Range[1], where you can quickly deploy a small lab to perform attack simulations. However, I will use two other projects throughout the book.

The first project I will use throughout the book is the GOADv2 lab created by Orange Cyberdefense[2]. To deploy it, you will need a Linux-based host OS with VMware Workstation or Oracle VirtualBox. It is also possible to deploy the lab on Proxmox, as...

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