What Is Active Directory Security and Penetration Testing?

Active Directory (AD) is one of the most critical pieces of infrastructure in a Microsoft-based enterprise network — the place where user identities, computers, servers, security groups and access rights are centrally managed. Most organisations today run their authentication, authorisation and access management through Active Directory.

Active Directory security and penetration testing is a comprehensive security assessment carried out to evaluate the security posture of the domain infrastructure, identify misconfigurations, and find the weaknesses an attacker could use for privilege escalation, lateral movement or to obtain Domain Administrator rights.

Testing covers far more than the domain controllers: user accounts, service accounts, Group Policy Objects (GPO), the Kerberos infrastructure, DNS services, LDAP, SMB, NTLM, Active Directory Certificate Services (AD CS) and domain security configuration are all analysed using genuine attacker techniques.

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

Why Should You Run an Active Directory Security Test?

When Active Directory is compromised, an attacker gains control not of a single user account but of the entire corporate network. Obtaining Domain Administrator rights can mean complete control over servers, client machines, file shares and critical systems.

A misconfigured Active Directory environment creates the following risks:

Compromise of Domain Administrator rights
Account takeover
Kerberos attacks
NTLM relay attacks
Pass-the-Hash attacks
Pass-the-Ticket attacks
Golden Ticket and Silver Ticket attacks
Unauthorised access and privilege escalation
Ransomware spreading across the domain
Manipulation of Group Policy Objects
Abuse of service accounts
Data leakage and loss of business continuity

Active Directory security is therefore one of the most critical components of any corporate cyber security strategy.

What Is the Active Directory Infrastructure?

Active Directory is the central directory service that provides user authentication, device management and access authorisation.

Its core components are:

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

Because Active Directory is the central authentication system of a corporate network, it is among the first targets an attacker goes after. Misconfiguration, weak password policy, incorrect permissions and legacy protocols can all lead to complete compromise of the domain.

SecureSys Active Directory security testing analyses not only known vulnerabilities but also the privilege escalation, lateral movement and credential theft techniques attackers use in real environments.

The principal risks assessed are:

Weak password policies
Poor management of privileged accounts
Unauthorised administrative rights
GPO misconfiguration
SMB and LDAP security gaps
Kerberos weaknesses
Active Directory Certificate Services (AD CS) vulnerabilities
Insecure service accounts
LLMNR and NetBIOS configuration
Legacy protocols (NTLMv1 and similar)
Inadequate network segmentation
Delegation misconfiguration

Kerberos Security Testing

Kerberos is the default authentication protocol in an Active Directory environment. Misconfiguration or weak service accounts can allow an attacker to obtain privileged access without ever knowing a user's password.

SecureSys Kerberos security analysis evaluates the following:

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 configuration
Kerberos encryption types

NTLM and LDAP Security

NTLM and LDAP services are still actively used in many organisations. Misconfigured NTLM or LDAP can allow an attacker to capture credentials and move further into the domain.

The principal checks performed:

NTLMv1 usage
NTLM relay protection
LDAP signing
LDAP channel binding
Anonymous LDAP
SMB signing
LDAP enumeration
LDAP authorisation controls

Pass-the-Hash (PtH) Attacks

In a Pass-the-Hash attack, the attacker authenticates to a system using the NTLM hash value without knowing the user's actual password.

SecureSys analysis evaluates:

Hash protection mechanisms
LSASS protection
Credential Guard
NTLM usage
Hash storage behaviour

Pass-the-Ticket (PtT) Attacks

In a Pass-the-Ticket attack, Kerberos tickets are captured and used to impersonate a user's privileges.

The technique poses a particularly critical risk for Domain Administrator accounts.

Areas analysed:

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: if the Kerberos KRBTGT account is compromised, the attacker can forge a valid ticket for any user they choose.

A successful Golden Ticket attack yields:

Domain Administrator access
Authorisation with no expiry
Control of the entire domain

SecureSys testing analyses KRBTGT security, password rotation and ticket validation processes.

Silver Ticket Attacks

Silver Ticket attacks target specific services rather than the domain as a whole.

By forging tickets for file servers, SQL Server, IIS or other service accounts, an attacker can gain unauthorised access to those particular services.

What Is Kerberoasting?

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

The attacker obtains service tickets and then performs offline password cracking against them.

Areas tested:

SPN accounts
Service accounts
Weak passwords
AES usage
RC4 usage
Managed service accounts

What Is AS-REP Roasting?

User accounts with "Do not require Kerberos preauthentication" enabled are exposed to AS-REP Roasting.

In that case the attacker can obtain the Kerberos response without knowing the user's password and mount an offline password cracking attack.

SecureSys assesses:

Preauthentication
User account configuration
AES support
Legacy accounts

LLMNR and NBT-NS Poisoning

LLMNR and NetBIOS Name Service (NBT-NS) are among the most frequently abused services on a corporate network.

On a misconfigured network an attacker can:

Harvest NTLM hashes
Perform SMB relay
Capture credentials

The principal checks performed:

LLMNR
NBT-NS
WPAD
SMB signing
DNS configuration

SMB Relay and NTLM Relay Attacks

SMB relay attacks redirect user authentication traffic to other systems, and are critical in a domain environment.

Scenarios analysed:

SMB signing
NTLM relay
LDAP relay
HTTP relay
RPC relay

BloodHound Analysis and Attack Paths

BloodHound is an advanced analysis method that maps users, groups, computers and permission relationships in an Active Directory environment to reveal the attack paths through which an adversary could reach Domain Administrator rights.

SecureSys uses BloodHound analysis to evaluate:

Attack paths
Shortest path to Domain Admin
Privilege escalation
Delegation abuse
ACL abuse
GPO abuse
Trust relationships

Active Directory Certificate Services (AD CS) Security

When Active Directory Certificate Services is misconfigured, it can give rise to the ESC (Enterprise Security Configuration) vulnerabilities that have become some of the most critical Active Directory attacks in recent years.

Areas analysed:

ESC1
ESC2
ESC3
ESC4
ESC6
ESC8
Certificate templates
Enrollment rights
PKI configuration

Group Policy (GPO) Security

Group Policy Objects centrally manage computer and user configuration across the domain.

Misconfigured GPOs can lead to:

Privilege escalation
Malware distribution
Security policy being altered

SecureSys analyses:

GPO delegation
GPO permissions
Startup scripts
Logon scripts
Scheduled tasks
Registry policy

Privileged Access and Service Account Analysis

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

The principal areas tested:

Domain Admin
Enterprise Admin
Schema Admin
Backup Operator
Account Operator
Service accounts
Managed service accounts
gMSA
Local Administrator
SID history

Lateral Movement Techniques

Attackers do not stop at a single compromised machine; they work to move on to other systems within the domain.

SecureSys evaluates the following techniques through 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 carried out with reference to the MITRE ATT&CK Enterprise framework.

The principal techniques analysed:

Initial access
Execution
Persistence
Privilege escalation
Credential access
Discovery
Lateral movement
Collection
Exfiltration
Command and control

This means we assess not only isolated technical vulnerabilities but the complete attack chain an adversary could follow in the real world.

The Active Directory Security Testing Process

SecureSys Active Directory security tests follow this methodology:

Scoping and planning
Active Directory inventory analysis
Review of the domain and forest structure
User, group and permission analysis
Kerberos and NTLM security checks
BloodHound attack path analysis
Service account and GPO review
Privilege escalation scenarios
Lateral movement simulation
AD CS and certificate infrastructure analysis
Risk assessment
Preparation of technical and executive reports
Remediation guidance and retest

Why SecureSys?

Active Directory security is not a matter of checking user accounts or domain controllers alone. A genuine assessment must cover authentication protocols, authorisation structures, service accounts, trust relationships, the certificate infrastructure and every attack path an adversary could take towards Domain Administrator rights.

At SecureSys we conduct Active Directory security testing in line with MITRE ATT&CK Enterprise, Microsoft Security Baselines and accepted industry best practice. By testing BloodHound attack paths, Kerberoasting, AS-REP Roasting, NTLM relay, AD CS security and privilege escalation scenarios under controlled conditions, we reveal not only the vulnerabilities that exist today but the attack chains they make possible.

The SecureSys Difference

Expert penetration testing under TSE TS 13638
Active Directory security assessment referenced against MITRE ATT&CK Enterprise
BloodHound attack path and privilege escalation analysis
Kerberos, NTLM, LDAP and SMB security testing
Kerberoasting, AS-REP Roasting, Pass-the-Hash and Golden Ticket scenarios
Active Directory Certificate Services (AD CS) security analysis
Group Policy, service account and privileged access controls
Comprehensive reporting at both technical and executive level
Risk prioritisation, actionable remediation guidance and retest support

Active Directory Security and Penetration Testing Service