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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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What this book covers

Chapter 1, Getting the Lab Ready and Attacking Exchange Server, provides an overview of the attack kill chain, shows you how to deploy the lab environment, and focuses on Exchange Server attack surfaces with practical examples.

Chapter 2, Defense Evasion, teaches you about evading Antimalware Scan Interface (AMSI) and AppLocker, PowerShell enhanced logging, Sysmon, and Event Tracing for Windows (ETW).

Chapter 3, Domain Reconnaissance and Discovery, is where you will learn how to perform reconnaissance in a domain, blend into environment traffic, and learn more about the internals of tools such as BloodHound and Microsoft Advanced Threat Analytics (ATA).

Chapter 4, Credential Access in a Domain, covers ways to obtain credentials in the domain environment by capturing the hash, coercing authentication, “roasting” Kerberos, reading clear-text passwords if Local Administrator Password Solution (LAPS) is misconfigured, and collecting hashes of gMSA accounts or of a whole domain via DCSync.

Chapter 5, Lateral Movement in Domain and Across Forests, shows how an adversary can maneuver across an environment by abusing different types of delegation, passing different types of credential materials, relaying captured hashes, as well as moving to other forests.

Chapter 6, Domain Privilege Escalation, is where we will focus on ways to elevate privileges in a domain by abusing misconfigured Access Control Lists (ACL), Group Policy Objects (GPO), and special built-in groups, as well as moving from a child domain to a parent domain.

Chapter 7, Persistence on Domain Level, shows techniques to establish persistence on the domain level by forging tickets and manipulating ACLs and objects, as well as on the domain controller itself by adding a Skeleton Key, malicious SSP, a registry backdoor, and so on.

Chapter 8, Abusing Active Directory Certificate Services, covers the fundamentals of Public Key Infrastructure (PKI) implementation by Microsoft, along with ways to steal certificates, escalate privileges in the domain, and achieve persistence on account and domain levels.

Chapter 9, Compromising Microsoft SQL Server, is where we will focus on how to attack SQL Server, including enumeration, privilege escalation, lateral movement, and persistence.

Chapter 10, Taking over WSUS and SCCM, provides an overview of IT support management software and ways to abuse its functionality, leading to a complete takeover of the whole environment.

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