Defining Testing Scope
Before beginning an Active Directory penetration test, the scope of testing must be clearly defined and written authorization obtained from responsible parties in the organization. The testing scope should cover specific domains, forests, organizational units, and critical systems that will be analyzed for vulnerabilities and misconfigurations.
Scope documentation includes a list of target domain controllers, exclusion criteria (protected systems, critical services), time windows for conducting work, and success metrics. A well-defined testing boundary reduces the risk of unintended impact on production systems and ensures focus on the most significant areas of the infrastructure.
- Obtain written authorization before commencing testing activities
- Establish escalation contacts and incident procedures for critical findings
- Coordinate acceptable time windows for active testing phases
Reconnaissance and Information Gathering Phase
Reconnaissance begins with information gathering about the Active Directory structure without using tools that may generate anomalies. Public sources, DNS records, open ports, and accessible services are analyzed. This phase identifies domain controllers, global catalogs, and other critical infrastructure components.
Passive analysis reveals the basic domain structure, operating system versions in use, and primary security systems such as firewalls and intrusion detection systems. This information is used to plan subsequent active testing without prematurely triggering defensive mechanisms.
- Analyze DNS zones and public WHOIS records
- Identify open ports and running services
- Determine OS and application versions from available metadata
Enumeration of Users, Groups, and Privileges
Following network access, detailed enumeration of users, groups, group memberships, and assigned privileges is conducted. Built-in Active Directory tools are used to query information about the organization structure, including protected groups, high-privileged users, and delegated authorities.
Analysis of privileged group memberships, such as Domain Admins, Enterprise Admins, and Schema Admins, reveals potential attack points. Special attention is given to unexpected memberships, dormant accounts, and rights assigned to service accounts that could be compromised to achieve domain-level privileges.
- Query domain tree and forest structure information
- Analyze membership in critical groups and roles
- Identify users with delegated authorities and permissions
Identification of Configuration Vulnerabilities
Testing identifies typical configuration weaknesses, such as weak password policies, absence of Multi-Factor Authentication for critical accounts, improper permission delegations, and misconfigured Group Policy Objects. The presence of known vulnerabilities in domain controller versions and infrastructure components is verified.
Analysis also includes review of change history, residual access rights for departed employees, unused service accounts, and systems left in insecure states. Particular attention is paid to authentication mechanisms and the possibility of executing attacks on credential access or privilege escalation.
- Review password policies and complexity requirements
- Analyze delegation configuration and permissions
- Test credential protection and authentication mechanisms
Analysis of Privilege Escalation Paths
Testing identifies possible paths to escalate privileges from regular user to domain administrator. Configuration allowing local privilege escalation on individual systems is analyzed, then how this access could be used to compromise accounts with domain-level rights.
Special attention is given to attack chains requiring multiple sequential steps: for example, using a misconfigured service to obtain local administrator access, then using that access to retrieve credentials that can be leveraged to attack the domain controller. In this way, even weak configuration errors on individual systems can lead to compromise of the entire infrastructure.
- Analyze privileged service configurations and accessibility
- Identify credentials and materials available on workstations
- Verify security mechanisms preventing privilege escalation
Assessment of Detection and Logging Mechanisms
The test evaluates the capability of monitoring systems to detect various types of attacks on Active Directory. Logging of unauthorized access attempts, security configuration changes, unauthorized use of privileged accounts, and suspicious network activity is verified.
Analysis includes verification of log completeness, detection time for various attack types, and incident response speed. Missing or misconfigured logging can conceal signs of compromise, allowing attackers to remain undetected in the system for extended periods while performing lateral movement across the network.
- Verify domain controller logging configuration
- Assess attack visibility in SIEM systems
- Analyze detection timeframes and response capabilities
Documentation of Results and Recommendations
Penetration test results are documented in a detailed report containing descriptions of identified vulnerabilities, their severity, and potential impact on infrastructure. Each finding includes information about the discovery method, precise location in the infrastructure, and reproduction steps.
The report contains prioritized remediation recommendations, beginning with critical issues requiring immediate attention. For each recommendation, specific actions needed, required resources, and possible impact on system availability are specified. The report conclusion includes overall assessment of Active Directory security posture and strategic directions for improvement.
- Classify vulnerabilities by severity and business impact
- Provide exact reproduction steps for each finding
- Include practical and measurable remediation recommendations