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You're reading from  Pentesting Active Directory and Windows-based Infrastructure

Product typeBook
Published inNov 2023
PublisherPackt
ISBN-139781804611364
Edition1st Edition
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Author (1)
Denis Isakov
Denis Isakov
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Denis Isakov

Denis Isakov is a passionate security professional with 10+ years of experience ranging from incident response to penetration testing. He worked in various industries, including banking and consultancy. Denis is specialized in offensive security with particular focus on Active Directory and adversary malware. He has earned a Master's degree in Information Systems and Technologies in 2012. Additionally, Denis has achieved an array of industry certifications ranging from OSCP to GXPN. Outside of computers, Denis enjoys sports and discovering new places.
Read more about Denis Isakov

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Preface

Almost every day we hear about new breaches, data leaks, or ransomware attacks. Cybercrime nowadays is a big business that constantly strives for improvement. It is no longer a one-man show; cybercriminals have their own methodology, tooling, and qualified staff. The way to defend against them is to understand how they attack, their tactics, and their techniques.

We will apply this approach against various products of the most popular software vendor – Microsoft. This book is focused purely on Windows-based infrastructure because on-premises infrastructure is still a big thing for most companies. In this book, I will take you through an attack kill chain against Active Directory (AD), Active Directory Certificate Services, Microsoft Exchange Server, Microsoft SQL Server, and System Center Configuration Manager (SCCM). During the process, you will be introduced to known tactics and techniques with a lot of hands-on exercises.

By the end of the book, you will be able to perform a hands-on comprehensive security assessment of Windows-based infrastructure. In addition, you will receive recommendations on how to detect adversary activity and remediation suggestions.

Who this book is for

This book is truly intended to be an all-in-one guide for security professionals who work with Windows-based infrastructure, especially AD. Penetration testers and red team operators will find practical attack scenarios that they may encounter during real-life assessments. Security and IT engineers, as well as blue teamers and incident responders, will benefit from detection and remediation guidelines. To get the most out of this book, you should have basic knowledge of Windows services and AD.

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.

To get the most out of this book

Software/hardware covered in the book

Operating system requirements

Windows Active Directory

Linux host

Windows Services – WSUS and AD CS

Kali virtual machine

Exchange Server

SQL Server

SCCM

Conventions used

There are a number of text conventions used throughout this book.

Code in text: Indicates code words in text, database table names, folder names, filenames, file extensions, pathnames, dummy URLs, user input, and Twitter handles. Here is an example: “MailSniper calculates the time difference between authentication attempt responses.”

Any command-line input or output is written as follows:

[InternetShortcut]
URL=any
WorkingDirectory=any
IconFile=\\192.168.56.100\%USERNAME%.icon
IconIndex=1

Bold: Indicates a new term, an important word, or words that you see on screen. For instance, words in menus or dialog boxes appear in bold. Here is an example: “We will cover attack detection and possible prevention measures, as well as offensive Operational Security (OpSec).”

Tips or important notes

Appear like this.

Get in touch

Feedback from our readers is always welcome.

General feedback: If you have questions about any aspect of this book, email us at customercare@packtpub.com and mention the book title in the subject of your message.

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Author (1)

author image
Denis Isakov

Denis Isakov is a passionate security professional with 10+ years of experience ranging from incident response to penetration testing. He worked in various industries, including banking and consultancy. Denis is specialized in offensive security with particular focus on Active Directory and adversary malware. He has earned a Master's degree in Information Systems and Technologies in 2012. Additionally, Denis has achieved an array of industry certifications ranging from OSCP to GXPN. Outside of computers, Denis enjoys sports and discovering new places.
Read more about Denis Isakov