Advanced Windows Active Directory Penetration Testing

Mastering Advanced Windows Active Directory Penetration Testing: A Comprehensive Guide for Security Professionals

Windows Active Directory (AD) remains a cornerstone of corporate IT infrastructure, making it a critical target for penetration testers and security professionals. Understanding how to exploit vulnerabilities in Active Directory is essential for identifying weaknesses and fortifying defenses. This course offers an in-depth exploration of advanced AD penetration testing techniques, equipping you with the knowledge and skills to assess and secure enterprise environments.

What You’ll Learn

This course is structured to take you from foundational concepts to advanced attack scenarios, all within a real-world simulation environment. Key learning outcomes include:

1. Active Directory Fundamentals
   • Gain a solid understanding of AD architecture, including user accounts, groups, and Domain Name System (DNS).
   • Learn how Domain Trusts and Kerberos Authentication work to facilitate enterprise operations.
2. OSINT and Initial Access Techniques
   • Use external OSINT tools to gather intelligence.
   • Execute Kerberos-based password spraying, NTLM relay attacks, and AS-REP Roasting.
3. Network and Domain Enumeration
   • Deploy tools like Dig, Nslookup, NetExec, and BloodHound to map networks and enumerate domains.
   • Analyze protocols and identify misconfigurations that could be exploited.
4. Privilege Escalation and Lateral Movement
   • Perform Kerberoasting and exploit Kerberos delegations.
   • Abuse misconfigured AD Access Control Lists (ACLs) and Certificate Services.
5. Persistence Techniques
   • Master Golden Ticket, Silver Ticket, and other persistence methods.
   • Explore cross-domain and cross-forest attacks to expand lateral movement.
6. Reporting and Communication
   • Learn how to document findings in professional penetration testing reports.
   • Provide actionable recommendations for clients to mitigate risks.

Why This Course Stands Out

Unlike typical penetration testing training, this course emphasizes exploiting domain features rather than software vulnerabilities. It replicates scenarios that mimic a real-world adversary’s progression—from gaining initial access to achieving domain dominance.

Tools and Techniques Covered

You’ll leverage cutting-edge tools and techniques throughout the course, including:

• Enumeration Tools: BloodHound, Dig, and Nslookup.
• Exploitation Frameworks: Responder, Impacket, and Hashcat.
• Advanced Protocol Abuse: Kerberos, NTLM, and LLMNR/NBNS.

Ideal Participants

This course is designed for professionals with prior experience in penetration testing or IT security, including:

• Penetration testers and ethical hackers.
• Red and Blue team members seeking offensive insights.
• System administrators aiming to secure their AD environments.
• Security enthusiasts eager to deepen their knowledge of AD vulnerabilities.

Requirements

To succeed in this course, participants should have:

• A solid foundation in Active Directory and networking concepts.
• Experience with command-line interfaces on Windows and Linux.
• Access to a computer with at least 32GB RAM and 300GB of free storage.

Key Takeaways

By the end of the course, you’ll be equipped to:

• Identify and exploit AD vulnerabilities effectively.
• Perform advanced attacks, such as abusing Certificate Services and cross-forest trust bypasses.
• Write comprehensive penetration testing reports to help clients address security gaps.

Windows Active Directory security remains a dynamic and evolving field. This course is a step toward mastering the intricacies of AD penetration testing, enabling you to stay ahead in safeguarding enterprise systems.

Take the leap to refine your skills and enhance your value as a security professional.