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Pentesting Active Directory and Windows-based Infrastructure
Pentesting Active Directory and Windows-based Infrastructure

Pentesting Active Directory and Windows-based Infrastructure: A comprehensive practical guide to penetration testing Microsoft infrastructure

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Pentesting Active Directory and Windows-based Infrastructure

Getting the Lab Ready and Attacking Exchange Server

Windows Active Directory is the de facto standard in most enterprises to run and support Windows-based networks. While centralized management brings convenience, it also introduces security risks. When carrying out their operations, malicious actors plan to achieve certain goals, and compromising Active Directory can help them do so. Active Directory’s default configuration is far from being secure. The best way to learn about Active Directory security is to execute attacks in a safe environment, trying to detect and prevent unwanted malicious activities.

Throughout the book, we will focus on the Active Directory kill chain, executing attacks and trying to detect as well as prevent them. This chapter will cover how to deploy a safe playground for such activities. We will use this lab throughout the book, later on adding extra services that will be covered in corresponding chapters about Active Directory Certificate Services...

Technical requirements

In this chapter, you will need to have access to the following:

  • VMware Workstation or Oracle VirtualBox with at least 16 GB of RAM, 10 CPU cores, and at least 115 GB of total space (more if you take snapshots)
  • A Linux-based host OS is strongly recommended
  • Vagrant installed with the plugin for the corresponding virtualization platform and Ansible

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...

Active Directory kill chain

What is Active Directory? In plain words, it is a hierarchically structured storage of object information. One of the main benefits is that Active Directory allows centralized management and authentication. Now, let us briefly discuss what the Cyber Kill Chain is. This framework was developed by Lockheed Martin and has a military background. It is a concept that identifies the structure of an attack. We can adapt Cyber Kill Chain concepts for Active Directory as in the diagram from infosecn1nja on GitHub[5]. It has several steps, but it always follows the same cycle – recon, compromise, lateral movement – just with more privileged access:

Figure 1.4 – Active Directory kill chain

Figure 1.4 – Active Directory kill chain

The focus of this book is Windows-based infrastructure and its services only, so themes such as local privilege escalation on the host, initial access, and external recon are out of the scope of this book. I will briefly explain...

Why we will not cover initial access and host-related topics

Initial access is a vital, early-stage step to compromise the target environment. However, this will not be covered in this book for the following reasons. To be honest, this theme is as wide as it is deep. It requires cross-field knowledge from different areas of IT as well as psychology, so it would require a separate book itself. Also, there is a high chance that at the moment of such a book being published, half of the attack vectors will be killed by implementing security solutions, such as Endpoint Detection and Response (EDR), and/or covered by a blue team’s comprehensive detection capabilities. The reason is that it is rapidly developing, full of private research that isn’t published. In general, to obtain stable initial access to the target environment, there are three main topics to take care of – a resilient and secure attack infrastructure, covert tooling with the required capabilities, and...

Attacking Exchange Server

Exchange Server is a collaboration server developed by Microsoft. Despite the fact that more and more companies are moving to the O365 cloud, there is still a good possibility that you will encounter on-premises deployment. Exchange has multiple useful features for end users, but it is also extremely difficult to develop all of them securely. In recent years, a lot of research has been published revealing critical vulnerabilities in its different components. Moreover, patches from Microsoft did not always completely fix these vulnerabilities, meaning that adversaries attempted to develop a one-day exploit by reverse engineering the patch and were able to find a suitable bypass. Considering that sometimes it is not possible for businesses to react in a timely manner to such rapidly changing situations, the chance of being compromised is quite high.

But what is the benefit for an adversary to compromise Exchange? First of all, a successful takeover gives...

Summary

In this chapter, we deployed our lab for future activities. We are lucky to have two outstanding free projects available for training and research purposes. After that, we discussed the Active Directory kill chain, vital steps to compromise the target environment, and what OpSec is. Then, we dived deeper into the assume breach model, showing solid hurdles that need to be overcome to achieve stable initial access. We covered three main attack vectors for Exchange Server: credential access, Zero2Hero exploits, and abuse of client-side software. In the next chapter, we will scratch the surface of the defense evasion theme. It is a broad and deep topic, which you will see eventually narrows down to the rule know your tooling.

Further reading

The following resources for further study will help you dive deeper into the attacks covered in the chapter:

  1. Splunk Attack Range – https://github.com/splunk/attack_range
  2. Orange Cyberdefense GOADv2 – https://github.com/Orange-Cyberdefense/GOAD
  3. Deploy GOADv2 on Proxmox – https://mayfly277.github.io/categories/proxmox/
  4. DetectionLab project – https://www.detectionlab.network/
  5. Active Directory kill chain diagram – https://github.com/infosecn1nja/AD-Attack-Defense
  6. Red team infrastructure wiki – https://github.com/bluscreenofjeff/Red-Team-Infrastructure-Wiki
  7. EDR bypass team – https://dispatch.redteams.fyi/red-team-edr-bypass-team/
  8. Assume breach model – https://www.redsiege.com/wp-content/uploads/2019/09/AssumedBreach-ABM.pdf
  9. Mind map to assess the security of Exchange Server – https://github.com/Orange-Cyberdefense/arsenal/blob/master/mindmap/Pentesting_MS_Exchange_Server_on_the_Perimeter...
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Key benefits

  • Find out how to attack real-life Microsoft infrastructure
  • Discover how to detect adversary activities and remediate your environment
  • Apply the knowledge you’ve gained by working on hands-on exercises
  • Purchase of the print or Kindle book includes a free PDF eBook

Description

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.

Who is this book for?

This book is for pentesters and red teamers, security and IT engineers, as well as blue teamers and incident responders interested in Windows infrastructure security. The book is packed with practical examples, tooling, and attack-defense guidelines to help you assess and improve the security of your real-life environments. To get the most out of this book, you should have basic knowledge of Windows services and Active Directory.

What you will learn

  • Understand and adopt the Microsoft infrastructure kill chain methodology
  • Attack Windows services, such as Active Directory, Exchange, WSUS, SCCM, AD CS, and SQL Server
  • Disappear from the defender's eyesight by tampering with defensive capabilities
  • Upskill yourself in offensive OpSec to stay under the radar
  • Find out how to detect adversary activities in your Windows environment
  • Get to grips with the steps needed to remediate misconfigurations
  • Prepare yourself for real-life scenarios by getting hands-on experience with exercises
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Table of Contents

12 Chapters
Chapter 1: Getting the Lab Ready and Attacking Exchange Server Chevron down icon Chevron up icon
Chapter 2: Defense Evasion Chevron down icon Chevron up icon
Chapter 3: Domain Reconnaissance and Discovery Chevron down icon Chevron up icon
Chapter 4: Credential Access in Domain Chevron down icon Chevron up icon
Chapter 5: Lateral Movement in Domain and Across Forests Chevron down icon Chevron up icon
Chapter 6: Domain Privilege Escalation Chevron down icon Chevron up icon
Chapter 7: Persistence on Domain Level Chevron down icon Chevron up icon
Chapter 8: Abusing Active Directory Certificate Services Chevron down icon Chevron up icon
Chapter 9: Compromising Microsoft SQL Server Chevron down icon Chevron up icon
Chapter 10: Taking Over WSUS and SCCM Chevron down icon Chevron up icon
Index Chevron down icon Chevron up icon
Other Books You May Enjoy Chevron down icon Chevron up icon

Customer reviews

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Rating distribution
Full star icon Full star icon Full star icon Full star icon Half star icon 4.9
(14 Ratings)
5 star 92.9%
4 star 7.1%
3 star 0%
2 star 0%
1 star 0%
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N/A Feb 21, 2024
Full star icon Full star icon Full star icon Full star icon Full star icon 5
Pubblicazioni interessanti scritti con il giusto livello tecnico ma soprattutto in modo chiaro.
Feefo Verified review Feefo
Vedant Gavde Dec 16, 2023
Full star icon Full star icon Full star icon Full star icon Full star icon 5
Denis Isakov's "Pentesting Active Directory and Windows-based Infrastructure" serves as an indispensable handbook for cybersecurity professionals and enthusiasts seeking to delve deep into the intricate realm of Windows-based infrastructure security. This book stands out for its focused exploration of lab environment setup and sophisticated evasion and penetration testing techniques specifically targeting Windows environments.From the outset, Isakov's approach is commendable. The book seamlessly introduces readers to the intricacies of setting up lab environments, laying a strong foundation for understanding and implementing effective penetration testing on Windows Active Directory. What makes this guide invaluable is its applicability not only to beginners but also as a comprehensive reference for seasoned professionals navigating the complexities of Windows-based infrastructure security.One of the book's notable strengths is its ability to make complex concepts accessible to a wide audience. Isakov's lucid explanations ensure that even intricate technical details are conveyed in an easy-to-understand manner. The clarity with which he articulates sophisticated evasion and pentesting techniques makes this book a go-to resource for anyone venturing into or honing their skills in this domain.The practicality of this guide cannot be overstated. Isakov skillfully intertwines real-world scenarios and practical examples throughout the book, offering hands-on experience and insights into tackling security challenges in Windows environments. This hands-on approach fosters a deeper understanding of the tools, methodologies, and tactics used in actual penetration testing scenarios.Having delved into "Pentesting Active Directory and Windows-based Infrastructure," I am convinced of its immense value in augmenting skills and techniques essential for securing Windows infrastructures. Whether you're a novice seeking to understand Windows penetration testing or an experienced professional looking to enhance your skill set, this book is an invaluable asset.In conclusion, Denis Isakov's "Pentesting Active Directory and Windows-based Infrastructure" is an essential guide that combines theory with practical application, making it a must-read for cybersecurity professionals aiming to elevate their knowledge and expertise in securing Windows-based networks.
Amazon Verified review Amazon
Amazon Customer May 23, 2024
Full star icon Full star icon Full star icon Full star icon Full star icon 5
I liked this book, as an experienced AD tester, it made me feel at home :)I think this book is a good resource for penetration testers, and I strongly recommend to replicate the techniques used in a lab environment, which is essential for practical learning and to master the concepts.I appreciated the coverage of topics such as defence evasion, reconnaissance, and domain privilege escalation from a windows environment perspective. I often test AD from windows, and don’t touch Kali. This knowledge will help you on real tests.And I liked the book touching on SCCM, Exchange, CS and MSSQL.However, like all resources, this book can’t cover everything. It serves as a robust foundation, and it is ultimately up to the reader to expand on the topics presented. The book is infact full of resources and links.For junior pentesters, the book may take longer to digest due to the complexity and depth of Active Directory. However, this should not discourage you, but trigger your curiosity and interest.For more experienced testers, it still holds value in my opinion, offering insights that can refine your existing knowledge. There is always something to learn, whether it is a new tool or a different way to achieve the same goal.A book to read, especially if you love Active Directory or if you want to get better at it.
Amazon Verified review Amazon
Victor kolawole May 25, 2024
Full star icon Full star icon Full star icon Full star icon Full star icon 5
This book has the best content when it comes to an active directory penetration testing, I never regretted buying this book, the hands-on labs are top notch and I will recommend it for anyone who want to learn more about active directory pentesting and it's environment.
Amazon Verified review Amazon
Ranjan Raja May 15, 2024
Full star icon Full star icon Full star icon Full star icon Full star icon 5
Very good book for absolute beginners who want to be expertise in penetration testing and cyber security .Good work author.
Amazon Verified review Amazon
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