deploying-active-directory-honeytokens

Imported from mukul975/anthropic-cybersecurity-skills (skills/deploying-active-directory-honeytokens/SKILL.md). Install upstream with npx skills add mukul975/anthropic-cybersecurity-skills --skill deploying-active-directory-honeytokens. Copyright stays with the author (Apache-2.0).

Deploying Active Directory Honeytokens

When to Use

• When deploying deception-based detection in Active Directory environments
• When detecting Kerberoasting attacks via fake SPN honeytokens (honeyroasting)
• When creating tripwire accounts to detect credential theft and lateral movement
• When building decoy GPOs to detect Group Policy Preference password harvesting
• When creating deceptive BloodHound paths to misdirect and detect attackers
• When supplementing existing AD monitoring with high-fidelity detection signals

Prerequisites

• Domain Admin or delegated AD administration privileges
• Active Directory domain (Windows Server 2016+ recommended)
• Windows Event Log forwarding to SIEM (Splunk, Sentinel, Elastic)
• PowerShell 5.1+ with ActiveDirectory module
• Group Policy Management Console (GPMC)
• Understanding of AD security, Kerberos, and BloodHound attack paths

Background

Why AD Honeytokens

Traditional signature-based detection misses novel attack techniques. Honeytokens provide high-fidelity detection with near-zero false positives because any interaction with a decoy object is inherently suspicious. In Active Directory:

• Fake privileged accounts detect credential dumping (DCSync, NTDS.dit extraction)
• Fake SPNs detect Kerberoasting reconnaissance (TGS requests for nonexistent services)
• Decoy GPOs detect Group Policy Preference password harvesting
• Fake BloodHound paths mislead attackers using graph-based AD analysis

Key Detection Event IDs

Making Honeytokens Realistic

Per Trimarc Security research, effective honeytokens must appear legitimate:

• Age the account: Repurpose old inactive accounts (10-15 year old accounts in similarly aged domains appear authentic)
• Set AdminCount=1: Flags the account as having elevated AD rights, making it an attractive Kerberoasting target
• Use realistic naming: Match organizational naming conventions (svc_sqlbackup, admin.maintenance, svc_exchange_legacy)
• Set old password date: Password age of 10+ years with an SPN looks like a high-value, neglected service account to attackers
• Add group memberships: Place in visible groups like "Remote Desktop Users" or a custom "Backup Operators" to increase attacker interest
• Avoid detection tells: Attackers check creation date vs. last logon vs. password change date for consistency

Instructions

Step 1: Deploy Fake Privileged Admin Account

Create a honeytoken account that mimics a legacy privileged service account.

# Import the deployment module
Import-Module .\scripts\Deploy-ADHoneytokens.ps1

# Create a honeytoken admin account
$honeyAdmin = New-HoneytokenAdmin `
    -SamAccountName "svc_sqlbackup_legacy" `
    -DisplayName "SQL Backup Service (Legacy)" `
    -Description "Legacy SQL Server backup service account - DO NOT DELETE" `
    -OU "OU=Service Accounts,DC=corp,DC=example,DC=com" `
    -PasswordLength 128 `
    -SetAdminCount $true

Write-Host "Honeytoken admin created: $($honeyAdmin.DistinguishedName)"

Step 2: Deploy Fake SPN for Kerberoasting Detection

Assign a realistic but fake SPN to the honeytoken account. Any TGS request for this SPN is definitively malicious (honeyroasting).

# Add fake SPN to honeytoken account
$honeySPN = Add-HoneytokenSPN `
    -SamAccountName "svc_sqlbackup_legacy" `
    -ServiceClass "MSSQLSvc" `
    -Hostname "sql-legacy-bak01.corp.example.com" `
    -Port 1433

Write-Host "Honey SPN registered: $($honeySPN.SPN)"
Write-Host "Monitor Event ID 4769 for TGS requests targeting this SPN"

Step 3: Deploy Decoy GPO with Credential Trap

Create a fake GPO in SYSVOL with an embedded cpassword (Group Policy Preference password). Attackers using tools like Get-GPPPassword or gpp-decrypt will find and attempt to use these credentials, triggering detection.

# Create decoy GPO with cpassword trap
$decoyGPO = New-DecoyGPO `
    -GPOName "Server Maintenance Policy (Legacy)" `
    -DecoyUsername "admin_maintenance" `
    -DecoyDomain "CORP" `
    -SYSVOLPath "\\corp.example.com\SYSVOL\corp.example.com\Policies" `
    -EnableAuditSACL $true

Write-Host "Decoy GPO created: $($decoyGPO.GPOGuid)"
Write-Host "SACL audit enabled - any read attempt will generate Event ID 4663"

Step 4: Create Deceptive BloodHound Paths

Set ACL permissions that create fake attack paths visible to BloodHound/SharpHound reconnaissance, leading attackers toward monitored honeytokens.

# Create fake BloodHound attack path
$deceptivePath = New-DeceptiveBloodHoundPath `
    -HoneytokenSamAccount "svc_sqlbackup_legacy" `
    -TargetHighValueGroup "Domain Admins" `
    -IntermediateOU "OU=Service Accounts,DC=corp,DC=example,DC=com"

Write-Host "Deceptive path created: $($deceptivePath.PathDescription)"

Step 5: Configure Detection Rules

Set up SIEM detection rules to alert on any honeytoken interaction.

# Using the Python detection agent
from agent import ADHoneytokenMonitor

monitor = ADHoneytokenMonitor(config_path="honeytoken_config.json")

# Register all honeytokens for monitoring
monitor.register_honeytoken("svc_sqlbackup_legacy", token_type="admin_account")
monitor.register_honeytoken("MSSQLSvc/sql-legacy-bak01.corp.example.com:1433", token_type="spn")
monitor.register_honeytoken("admin_maintenance", token_type="gpo_credential")

# Generate SIEM detection rules
splunk_rules = monitor.generate_detection_rules(siem="splunk")
sentinel_rules = monitor.generate_detection_rules(siem="sentinel")
sigma_rules = monitor.generate_detection_rules(siem="sigma")

for rule in sigma_rules:
    print(f"Rule: {rule['title']}")
    print(f"  Detection: {rule['detection_logic']}")

Step 6: Validate Deployment

Test the honeytokens to ensure detection fires correctly.

# Validate honeytoken deployment
$validation = Test-HoneytokenDeployment `
    -SamAccountName "svc_sqlbackup_legacy" `
    -ValidateAdminCount `
    -ValidateSPN `
    -ValidateGPODecoy `
    -ValidateAuditPolicy

$validation | Format-Table Check, Status, Details -AutoSize

Examples

Full Deployment Pipeline

Import-Module .\scripts\Deploy-ADHoneytokens.ps1

# Deploy complete honeytoken suite
$deployment = Deploy-FullHoneytokenSuite `
    -Environment "Production" `
    -ServiceAccountOU "OU=Service Accounts,DC=corp,DC=example,DC=com" `
    -SYSVOLPath "\\corp.example.com\SYSVOL\corp.example.com\Policies" `
    -TokenCount 3 `
    -IncludeSPN $true `
    -IncludeGPODecoy $true `
    -IncludeBloodHoundPath $true `
    -SIEMType "Splunk"

# Output deployment report
$deployment.Tokens | Format-Table Name, Type, SPN, DetectionRule -AutoSize
$deployment | Export-Csv "honeytoken_deployment_report.csv" -NoTypeInformation

Kerberoasting Detection Query (Splunk)

index=wineventlog EventCode=4769 ServiceName="svc_sqlbackup_legacy"
| eval alert_severity="critical"
| eval alert_type="honeytoken_kerberoast"
| table _time, src_ip, Account_Name, ServiceName, Ticket_Encryption_Type
| sort - _time

Microsoft Sentinel KQL Detection

SecurityEvent
| where EventID == 4769
| where ServiceName in ("svc_sqlbackup_legacy", "svc_exchange_legacy")
| extend AlertType = "Honeytoken Kerberoast Detected"
| project TimeGenerated, Computer, Account, ServiceName, IpAddress, TicketEncryptionType

References

• Trimarc Security - The Art of the Honeypot Account: https://www.hub.trimarcsecurity.com/post/the-art-of-the-honeypot-account-making-the-unusual-look-normal
• ADSecurity.org - Detecting Kerberoasting Activity Part 2 (Honeypot): https://adsecurity.org/?p=3513
• Microsoft Defender for Identity Honeytokens: https://techcommunity.microsoft.com/blog/microsoftthreatprotectionblog/deceptive-defense-best-practices-for-identity-based-honeytokens-in-microsoft-def/3851641
• SpecterOps - Kerberoasting and AES-256: https://specterops.io/blog/2025/10/21/is-kerberoasting-still-a-risk-when-aes-256-kerberos-encryption-is-enabled/
• APT29a Blog - Deploying Honeytokens in AD: https://apt29a.blogspot.com/2019/11/deploying-honeytokens-in-active.html
• ADSecurity.org - Detecting Kerberoasting Activity: https://adsecurity.org/?p=3458