What Is an Active Directory Security and Penetration Test?

Active Directory (AD) is one of the most critical infrastructures in Microsoft-based enterprise networks, where user identities, computers, servers, security groups, and access permissions are centrally managed. Today, the vast majority of organizations conduct their authentication, authorization, and access management processes through Active Directory.

An Active Directory Security and Penetration Test (Active Directory Penetration Test) is a comprehensive security test conducted to assess the security level of the domain infrastructure, identify misconfigurations, and determine security vulnerabilities that attackers could exploit to achieve privilege escalation, lateral movement or to gain Domain Administrator privileges.

During the testing process, we examine not only Domain Controllers but also but also user accounts, service accounts, Group Policy (GPO), the Kerberos infrastructure, DNS services, LDAP, SMB, NTLM, Active Directory Certificate Services (AD CS), and domain security configurations are analyzed using real-world attacker techniques.

SecureSys Active Directory Security Tests are conducted in accordance with MITRE ATT&CK, Microsoft Security Baselines, NIST, PTES, and Microsoft Active Directory Security Best Practices.

Why Should an Active Directory Security Test Be Performed?

When the Active Directory infrastructure is compromised, attackers can gain control not only of a single user account but of the entire corporate network. Gaining Domain Administrator privileges can result in complete control over servers, client computers, file shares, and critical systems.

An improperly configured Active Directory environment can pose the following risks:

Compromise of Domain Administrator privileges
Compromise of user accounts
Kerberos attacks
NTLM relay attacks
Pass-the-hash attacks
Pass-the-Ticket attacks
Golden Ticket and Silver Ticket attacks
Unauthorized Access and Privilege Escalation
Spread of ransomware within the domain
Manipulation of Group Policy Objects (GPOs)
Misuse of service accounts
Data leaks and disruption of business continuity

For this reason, Active Directory security is one of the most critical components of an enterprise cybersecurity strategy.

What Is the Active Directory Infrastructure?

Active Directory is a centralized directory service that provides user authentication, device management, and access authorization.

The key components are as follows:

Domain Controller (DC)
Forest
Domain
Organizational Unit (OU)
Group Policy Objects (GPO)
DNS
LDAP
Kerberos
NTLM
Active Directory Certificate Services (AD CS)
Active Directory Federation Services (AD FS)
Group-Managed Service Accounts (gMSA)

Active Directory Vulnerabilities

Since Active Directory infrastructures serve as the central authentication system for corporate networks, they are one of the primary targets for attackers. Misconfigurations, weak password policies, improper authorizations, and outdated protocols can lead to the complete compromise of the domain.

As part of SecureSys Active Directory Security Testing, we analyze not only known vulnerabilities but also privilege escalation, lateral movement, and credential theft techniques actually used by attackers in real-world environments.

Key security risks assessed:

Weak password policies
Improper management of privileged accounts
Unauthorized administrative privileges
GPO configuration errors
SMB and LDAP security vulnerabilities
Kerberos vulnerabilities
Active Directory Certificate Services (AD CS) vulnerabilities
Insecure service accounts
LLMNR and NetBIOS configurations
Legacy protocols (NTLMv1, etc.)
Lack of network segmentation
Delegation configuration errors

Kerberos Security Tests

Kerberos is the default authentication protocol in Active Directory environments. Incorrect configurations or weak service accounts can allow attackers to gain privileged access without directly knowing user passwords.

In Kerberos security analyses conducted by SecureSys, the following controls are evaluated:

Kerberos Ticket Security
Ticket Granting Ticket (TGT)
Service Ticket Analysis
Kerberos Delegation
Constrained Delegation
Unconstrained Delegation
Resource-Based Constrained Delegation (RBCD)
Ticket Lifetime
AES / RC4 Configurations
Kerberos Encryption Types

NTLM and LDAP Security

NTLM and LDAP services are still actively used in many organizations. Improperly configured NTLM or LDAP services can allow attackers to compromise credentials and move laterally within the domain.

Key controls tested:

Use of NTLMv1
NTLM Relay Protection
LDAP Signing
LDAP Channel Binding
Anonymous LDAP
SMB Signing
LDAP Enumeration
LDAP Authentication Checks

Pass-the-Hash (PtH) Attacks

In Pass-the-Hash attacks, an attacker can authenticate to the system using the NTLM hash value without knowing the user’s actual password.

In SecureSys analyses:

Hash Protection Mechanisms
LSASS Protection
CredentialGuard
NTLM Usage
Hash Storage Behaviors

are being evaluated.

Pass-the-Ticket (PtT) Attacks

In Pass-the-Ticket attacks, Kerberos tickets are compromised to impersonate user privileges.

This technique poses a critical risk, particularly for Domain Administrator accounts.

Topics analyzed:

Ticket Security
TGT Protection
Service Ticket Security
Ticket Lifetime
Ticket Reuse

Golden Ticket Attacks

A Golden Ticket attack is one of the most critical Active Directory attacks, allowing an attacker to generate a valid ticket for any desired user account if a Kerberos KRBTGT account is compromised.

When this attack is successful,

Domain Administrator access
Permanent authorization
Complete control over the domain

can be obtained.

In SecureSystests, KRBTGT security, password rotation, and ticket validation processes are analyzed.

Silver Ticket Attacks

In Silver Ticket attacks, only specific services are targeted.

By generating tickets associated with file servers, SQL Server, IIS, or other service accounts, unauthorized access to the relevant services can be gained.

What Is Kerberoasting?

Kerberoasting is a Kerberos-based attack that targets service accounts defined by Service Principal Name (SPN).

By obtaining service tickets, an attacker can perform offline password cracking.

Tested headings:

SPN Accounts
Service Accounts
Weak Passwords
AES Usage
RC4 Usage
ManagedServiceAccount

What Is AS-REP Roasting?

User accounts with the "Do not require Kerberos pre-authentication" option enabled may be vulnerable to an AS-REP Roasting attack.

In this scenario, an attacker can obtain the Kerberos response without knowing the user’s password and carry out an offline password cracking attack.

SecureSys;

Preauthentication
User Configurations
AES Support
Legacy Accounts

performs a security assessment on these.

LLMNR and NBT-NS Poisoning

LLMNR and NetBIOS Name Service (NBT-NS) are among the most frequently exploited services in corporate networks.

In misconfigured networks, an attacker can

NTLM Hashing
SMB Relay
credential theft

operations.

Key controls analyzed:

LLMNR
NBT-NS
WPAD
SMBSigning
DNS Configurations

SMB Relay and NTLM Relay Attacks

SMB relay attacks are critical attacks that allow user authentication traffic to be redirected to other systems.

In the tests:

SMBSigning
NTLM Relay
LDAP Relay
HTTPRelay
RPCRelay

scenarios are analyzed.

BloodHound Analysis and Attack Path

BloodHound is an advanced analysis method that identifies potential attack paths (AttackPath) through which attackers could gain Domain Administrator privileges by analyzing users, groups, computers, and authorization relationships within an Active Directory environment.

In SecureSystests, BloodHound analyses are used to:

AttackPath
Shortest Path to Domain Admin
Privilege Escalation
Delegation Abuse
ACL Abuse
GPO Abuse
Trust Relationship

is being evaluated.

Active Directory Certificate Services (AD CS) Security

If Active Directory Certificate Services is misconfigured, it can lead to ESC (Enterprise Security Configuration) vulnerabilities, which are among the most critical Active Directory attacks in recent years.

Topics analyzed:

ESC1
ESC2
ESC3
ESC4
ESC6
ESC8
CertificateTemplate
EnrollmentRights
PKI Configurations

Group Policy (GPO) Security

Group Policy Objects (GPO) centrally manage computer and user configurations across the domain.

Improperly configured GPOs;

Privilege Escalation
Malware distribution
Alteration of security policies

By SecureSys;

GPODelegation
GPOPermission
StartupScript
LogonScript
ScheduledTask
RegistryPolicy

is being analyzed.

Privileged Access and Service Account Analysis

Service accounts and privileged users are among the most critical components of Active Directory.

Key areas tested:

Domain Admin
Enterprise Admin
Schema Admin
Backup Operator
Account Operator
ServiceAccount
ManagedServiceAccount
gMSA
LocalAdministrator
SIDHistory

Lateral Movement Techniques

Attackers do not stop at compromising a single computer; they attempt to move laterally to other systems within the domain.

SecureSys evaluates the following techniques using controlled scenarios:

Pass-the-Hash
Pass-the-Ticket
PsExec
WMI
WinRM
RDP
SMB
Remote Service Creation
Scheduled Tasks
DCOM
Remote PowerShell

MITRE ATT&CK and Active Directory

SecureSys Active Directory Security Tests are conducted in accordance with the MITRE ATT&CK Enterprise Framework.

Key techniques analyzed:

InitialAccess
Execution
Persistence
Privilege Escalation
CredentialAccess
Discovery
Lateral Movement
Collection
Exfiltration
Command and Control

This way, we assess not only technical vulnerabilities but also the entire attack chain (AttackChain) that attackers could follow in the real world.

Active Directory Security Testing Process

SecureSys Active Directory Security Tests are conducted using the following methodology:

Scope Definition and Planning
Active Directory Inventory Analysis
Examination of Domain and Forest Structure
User, Group, and Permission Analysis
Kerberos and NTLM Security Checks
BloodHound Attack Path Analysis
Service Accounts and GPO Review
Privilege Escalation Scenarios
Lateral Movement Simulations
AD CS and Certificate Infrastructure Analysis
Risk Assessment
Preparation of Technical and Management Reports
Recommendations for Improvement and Retesting

Why SecureSys?

Active Directory security is not limited to simply checking user accounts or Domain Controllers. A true security assessment must cover authentication protocols, authorization structures, service accounts, trust relationships, the certificate infrastructure, and all attack vectors that an attacker could use to gain Domain Administrator privileges.

At SecureSys, we conduct Active Directory security tests in accordance with MITRE ATT&CK Enterprise, Microsoft Security Baselines, and industry-accepted best practices.By conducting controlled tests of BloodHound Attack Path analyses, Kerberoasting, AS-REPRoasting, NTLM Relay, AD CS security, and privilege escalation scenarios, we uncover not only existing vulnerabilities but also potential attack chains.

The SecureSys Difference

Expert penetration testing service in accordance with TSE TS 13638
Active Directory security assessment based on the MITRE ATT&CK Enterprise framework
BloodHound Attack Path and Privilege Escalation analyses
Kerberos, NTLM, LDAP, and SMB security tests
Kerberoasting, AS-REPRoasting, Pass-the-Hash, and Golden Ticket scenarios
Active Directory Certificate Services (AD CS) security analysis
Group Policy (GPO), service accounts, and privileged access controls
Comprehensive reporting at both the technical and administrative levels
Risk prioritization, actionable remediation recommendations, and retest support

Active Directory Security and Penetration Testing Service