Penetration Testing and Exploitation of Active Directory Configuration Vulnerabilities

The primary objective of this paper is to do comprehensive internal penetration testing on a system that incorporates the most recent security updates and utilizes the Active Directory service. This paper systematically delineates various established methodologies for reconnaissance, enumeration, privilege escalation, and persistence within Active Directory environments. In this research's empirical segment, specific privilege escalation techniques were employed, notably the NTLM relay attack and the Kerberos Resource-based Constrained Delegation attack. Additionally, this study explores methodologies for securing prolonged access to the system, such as leveraging the Directory Services Restore Mode (DSRM) password associated with the local Administrator and extracting user password hashes by duplicating the NTDS.dit database. These techniques are critical for understanding the robustness of the security framework in Active Directory environments and identifying potential vulnerabilities that malicious entities could exploit.