Getting Started with Active Directory Pentesting

Welcome to the Active Directory (AD) pentesting section of the documentation. This guide introduces the fundamentals of pentesting Active Directory environments, a critical skill for security professionals aiming to identify and mitigate vulnerabilities in enterprise networks.

What is Active Directory Pentesting?

Active Directory is Microsoft’s directory service that manages authentication, authorization, and resource access in Windows-based networks. Pentesting AD involves assessing the security of AD configurations, user accounts, permissions, and infrastructure to uncover weaknesses that attackers could exploit.

This section focuses on practical techniques, tools, and methodologies for AD pentesting, including reconnaissance, privilege escalation, and lateral movement.

Why Pentest Active Directory?

AD is the backbone of many enterprise environments, making it a prime target for attackers. A single misconfiguration can lead to domain compromise, data breaches, or ransomware deployment. Pentesting AD helps organizations:

• Identify weak passwords and misconfigured accounts.
• Detect excessive permissions or insecure group policies.
• Harden domain controllers and related infrastructure.
• Prepare for real-world attack scenarios, such as pass-the-hash or Kerberos-based attacks.

What’s Covered in This Section

The Active Directory pentesting documentation is organized to guide you from beginner concepts to advanced techniques:

• Reconnaissance: Learn how to gather information about AD environments using tools like BloodHound and PowerView.
• Enumeration: Discover users, groups, and permissions to identify potential attack paths.
• Exploitation: Explore techniques like Kerberoasting, NTLM relay, and privilege escalation.
• Post-Exploitation: Understand lateral movement, persistence, and data exfiltration in AD.

Getting Started

To begin pentesting Active Directory, you’ll need:

1. A Lab Environment: Set up a safe, isolated AD lab using virtual machines (e.g., with VMware or VirtualBox). Tools like Microsoft’s AD DS Deployment Guide can help.

2. Pentesting Tools: Install tools like:

   • Impacket for protocol attacks.
   • BloodHound for AD relationship mapping.
   • Mimikatz for credential extraction.

3. Basic Knowledge: Familiarity with Windows networking, LDAP, and Kerberos is helpful but not required. Start with our Guides for foundational knowledge.

Next Steps

Explore the following sections of the documentation to deepen your AD pentesting skills:

• Guides: Step-by-step tutorials on AD concepts and pentesting workflows.
• OSINT: Learn how open-source intelligence complements AD reconnaissance.