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

Enhance your skill set to pentest against real-world Microsoft infrastructure with hands-on exercises and by following attack/detect guidelines with OpSec considerationsKey FeaturesFind out how to attack real-life Microsoft infrastructureDiscover how to detect adversary activities and remediate your environmentApply the knowledge you've gained by working on hands-on exercisesBook DescriptionThis 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.What you will learnUnderstand and adopt the Microsoft infrastructure kill chain methodologyAttack Windows services, such as Active Directory, Exchange, WSUS, SCCM, AD CS, and SQL ServerDisappear from the defender's eyesight by tampering with defensive capabilitiesUpskill yourself in offensive OpSec to stay under the radarFind out how to detect adversary activities in your Windows environmentGet to grips with the steps needed to remediate misconfigurationsPrepare yourself for real-life scenarios by getting hands-on experience with exercisesWho this book is forThis 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.About the AuthorDenis 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. Table of ContentsGetting the Lab Ready and Attacking Exchange ServerDefense EvasionDomain Reconnaissance and DiscoveryCredential Access in DomainLateral Movement in Domain and Across ForestsDomain Privilege EscalationPersistence on Domain LevelAbusing Active Directory Certificate ServicesCompromising Microsoft SQL ServerTaking over WSUS and SCCM