When to Use

Workflow

Step 1: Deploy Canary Files on File Shares

Place canary files in strategic locations that ransomware will encounter during encryption:

# Deploy canary files across all file shares
# Files are named to appear early in alphabetical and directory order
# Ransomware typically encrypts alphabetically or by directory traversal

$shares = @("\\fileserver01\finance", "\\fileserver01\hr", "\\fileserver01\engineering")
$canaryNames = @(
    "!_IMPORTANT_DO_NOT_DELETE.docx",
    "000_Budget_2026_FINAL.xlsx",
    "_Confidential_Employee_Records.pdf",
    "AAAA_Quarterly_Report.docx"
)

foreach ($share in $shares) {
    foreach ($name in $canaryNames) {
        $targetPath = Join-Path $share $name
        # Create a legitimate-looking file with canary content
        # The file contains a unique token that triggers on access
        $content = "This document contains confidential financial data.`n"
        $content += "Q4 2025 Revenue: $42.3M | Q1 2026 Forecast: $45.1M`n"
        $content += "Prepared by: Finance Department`n"
        Set-Content -Path $targetPath -Value $content
        # Set file as hidden system to avoid user interaction
        $file = Get-Item $targetPath
        $file.Attributes = [System.IO.FileAttributes]::Hidden
    }
}

# Also deploy in subdirectories (ransomware traverses recursively)
$subDirs = Get-ChildItem -Path "\\fileserver01\finance" -Directory -Recurse | Select-Object -First 20
foreach ($dir in $subDirs) {
    $canaryPath = Join-Path $dir.FullName "!_Budget_Summary.xlsx"
    Set-Content -Path $canaryPath -Value "Canary file for ransomware detection"
    (Get-Item $canaryPath).Attributes = [System.IO.FileAttributes]::Hidden
}

Step 2: Configure File Integrity Monitoring on Canary Files

Windows FSRM approach:

# Configure FSRM to monitor for ransomware file extensions
# and canary file modifications

Install-WindowsFeature -Name FS-Resource-Manager -IncludeManagementTools

# Create file screen for known ransomware extensions
$ransomExtensions = @(
    "*.encrypted", "*.locked", "*.crypto", "*.crypt",
    "*.locky", "*.cerber", "*.zepto", "*.thor",
    "*.aesir", "*.zzzzz", "*.wallet", "*.onion",
    "*.wncry", "*.wcry", "*.lockbit", "*.BlackCat",
    "*.ALPHV", "*.rhysida", "*.play"
)

# Create file group for ransomware extensions
New-FsrmFileGroup -Name "Ransomware_Extensions" -IncludePattern $ransomExtensions

# Create file screen template
New-FsrmFileScreenTemplate -Name "Ransomware_Screen" `
    -IncludeGroup "Ransomware_Extensions" `
    -Active:$false  # Passive mode: alert without blocking

# Apply to all monitored shares
$monitoredPaths = @("D:\Shares\Finance", "D:\Shares\HR", "D:\Shares\Engineering")
foreach ($path in $monitoredPaths) {
    New-FsrmFileScreen -Path $path -Template "Ransomware_Screen"
}

Canary file modification monitoring with PowerShell FileSystemWatcher:

# Real-time canary file monitoring service
$canaryPaths = @(
    "D:\Shares\Finance\!_IMPORTANT_DO_NOT_DELETE.docx",
    "D:\Shares\HR\000_Budget_2026_FINAL.xlsx",
    "D:\Shares\Engineering\_Confidential_Employee_Records.pdf"
)

$watcher = New-Object System.IO.FileSystemWatcher
$watcher.Path = "D:\Shares"
$watcher.Filter = "*"
$watcher.IncludeSubdirectories = $true
$watcher.EnableRaisingEvents = $true

$action = {
    $path = $Event.SourceEventArgs.FullPath
    $changeType = $Event.SourceEventArgs.ChangeType
    $timestamp = $Event.TimeGenerated

    # Check if modified file is a canary
    $isCanary = $false
    foreach ($canary in $canaryPaths) {
        if ($path -eq $canary) { $isCanary = $true; break }
    }

    if ($isCanary -or $changeType -eq "Renamed") {
        $alertMsg = "RANSOMWARE ALERT: Canary file modified! Path: $path | Change: $changeType | Time: $timestamp"
        # Log to Windows Event Log
        Write-EventLog -LogName Application -Source "RansomwareCanary" `
            -EventID 9999 -EntryType Error -Message $alertMsg
        # Send SIEM alert via syslog
        # Trigger automated containment
    }
}

Register-ObjectEvent $watcher "Changed" -Action $action
Register-ObjectEvent $watcher "Deleted" -Action $action
Register-ObjectEvent $watcher "Renamed" -Action $action

Step 3: Deploy Honeypot Network Shares

Create decoy file shares that appear to contain high-value data:

# Create honeypot share on dedicated server
# This server monitors ALL file access and alerts on any activity

New-Item -Path "D:\HoneypotShares\Executive_Compensation" -ItemType Directory
New-Item -Path "D:\HoneypotShares\M&A_Documents" -ItemType Directory
New-Item -Path "D:\HoneypotShares\Board_Meeting_Notes" -ItemType Directory
New-Item -Path "D:\HoneypotShares\Customer_Database_Exports" -ItemType Directory

# Share with broad read access (enticing to attackers)
New-SmbShare -Name "Executive_Compensation" `
    -Path "D:\HoneypotShares\Executive_Compensation" `
    -FullAccess "DOMAIN\Domain Users" `
    -Description "Executive Compensation Files - Restricted"

# Populate with realistic-looking but fake documents
# Use document templates that look legitimate
$docContent = @"
CONFIDENTIAL - Executive Compensation Summary
FY 2026 Base Salary and Bonus Structures
CEO: [REDACTED] | CFO: [REDACTED] | CTO: [REDACTED]
Total Compensation Package: See Appendix A
"@
Set-Content -Path "D:\HoneypotShares\Executive_Compensation\FY2026_Comp_Summary.txt" -Value $docContent

# Enable detailed audit logging on honeypot share
$acl = Get-Acl "D:\HoneypotShares"
$auditRule = New-Object System.Security.AccessControl.FileSystemAuditRule(
    "Everyone", "ReadAndExecute,Write,Delete", "ContainerInherit,ObjectInherit",
    "None", "Success,Failure"
)
$acl.AddAuditRule($auditRule)
Set-Acl "D:\HoneypotShares" $acl

# Enable object access auditing via GPO
auditpol /set /subcategory:"File System" /success:enable /failure:enable

Step 4: Deploy Thinkst Canary Tokens

For organizations using Thinkst Canary or the free canarytokens.org service:

# Generate canary tokens via API (Thinkst Canary)
# These trigger alerts when documents are opened or URLs are accessed

# Word document token
curl -X POST "https://CONSOLE.canary.tools/api/v1/canarytoken/create" \
  -d "auth_token=YOUR_API_TOKEN" \
  -d "memo=Finance_Share_Canary" \
  -d "kind=doc-msword" \
  -o /tmp/canary_budget_report.docx

# PDF document token
curl -X POST "https://CONSOLE.canary.tools/api/v1/canarytoken/create" \
  -d "auth_token=YOUR_API_TOKEN" \
  -d "memo=HR_Share_Canary" \
  -d "kind=pdf-acrobat-reader" \
  -o /tmp/canary_employee_handbook.pdf

# Windows folder token (alerts when folder is browsed)
curl -X POST "https://CONSOLE.canary.tools/api/v1/canarytoken/create" \
  -d "auth_token=YOUR_API_TOKEN" \
  -d "memo=Executive_Folder_Browse" \
  -d "kind=windows-dir"

# Deploy Canary appliance (emulates a file server)
# Configure via web console to appear as:
# - Windows file server with SMB shares
# - Contains realistic-looking directories
# - Any access triggers immediate alert with source IP and activity details

Step 5: Integrate Alerts with SIEM and Automated Response

# siem_integration.py - Forward honeypot alerts to SIEM and trigger containment

import json
import requests
import logging
from datetime import datetime

SIEM_WEBHOOK = "https://siem.company.com/api/alerts"
NAC_API = "https://nac.company.com/api/v1/quarantine"
EDR_API = "https://edr.company.com/api/v1/isolate"

def send_ransomware_alert(source_ip: str, canary_path: str, action: str):
    """Send high-priority alert to SIEM and trigger automated containment."""
    alert = {
        "timestamp": datetime.utcnow().isoformat(),
        "severity": "CRITICAL",
        "category": "Ransomware - Canary File Triggered",
        "source_ip": source_ip,
        "canary_file": canary_path,
        "action_detected": action,
        "automated_response": "Host isolation initiated",
        "mitre_technique": "T1486 - Data Encrypted for Impact",
    }

    # Send to SIEM
    try:
        requests.post(SIEM_WEBHOOK, json=alert, timeout=5)
    except requests.RequestException as e:
        logging.error(f"SIEM alert failed: {e}")

    # Automated containment - isolate host via NAC
    try:
        requests.post(f"{NAC_API}/{source_ip}",
                      json={"action": "quarantine", "reason": "Ransomware canary triggered"},
                      timeout=5)
    except requests.RequestException as e:
        logging.error(f"NAC quarantine failed: {e}")

    # Automated containment - isolate host via EDR
    try:
        requests.post(EDR_API,
                      json={"ip": source_ip, "action": "isolate"},
                      timeout=5)
    except requests.RequestException as e:
        logging.error(f"EDR isolation failed: {e}")

    logging.critical(f"RANSOMWARE CANARY ALERT: {source_ip} modified {canary_path} ({action})")

Key Concepts

Tools & Systems

• Thinkst Canary: Commercial deception platform providing canary appliances (emulate servers) and canary tokens (trackable documents)
• Canarytokens.org: Free service from Thinkst for generating basic canary tokens (Word docs, PDFs, URLs, DNS)
• OpenCanary: Open-source honeypot daemon that emulates common services (SMB, RDP, SSH) and logs access attempts
• FSRM (File Server Resource Manager): Windows Server built-in tool for file screening, quota management, and ransomware extension detection
• Elastic Endpoint: Uses canary files internally for ransomware protection, triggering behavioral alerts on canary modification

Common Scenarios

Scenario: Early Detection of BlackByte Ransomware via Canary Files

Context: A retail company deploys canary files across 200 file shares and 3 honeypot shares. At 3:00 AM on a Saturday, the canary monitoring system generates 47 alerts in rapid succession as canary files across 12 shares are modified within 90 seconds.

Approach:

1. Canary file alert triggers automated containment: source workstation (10.2.8.55) quarantined via NAC within 30 seconds
2. SIEM correlation shows the source workstation had EDR alerts for PsExec execution 2 hours earlier (missed by overnight SOC)
3. Additional canary alerts from 3 other workstations indicate the ransomware is spreading via scheduled tasks
4. IR team isolates the affected VLAN, preventing encryption of the remaining 188 file shares
5. The 12 affected shares are restored from immutable backups within 4 hours
6. Estimated damage prevented: $2.3M in downtime and recovery costs based on the 95% of shares protected

Pitfalls:

• Placing canary files only in root directories where ransomware may skip them by targeting subdirectories first
• Using obvious canary names that sophisticated ransomware may recognize and avoid
• Not testing canary alerting end-to-end, discovering during an actual incident that alerts are not reaching the SOC
• Generating excessive canary alerts during legitimate file migrations or antivirus scans, causing alert fatigue

Output Format

## Ransomware Honeypot Deployment Report

**Organization**: [Name]
**Deployment Date**: [Date]

### Canary File Deployment
| Share | Files Deployed | Naming Convention | Alert Method |
|-------|---------------|-------------------|--------------|
| [Share path] | [Count] | [Pattern] | [FSRM/Watcher/Token] |

### Honeypot Shares
| Share Name | Location | Apparent Content | Monitoring |
|-----------|----------|-----------------|------------|
| [Name] | [Server] | [Description] | [Audit/Canary] |

### Alert Integration
- SIEM: [Connected/Not Connected]
- Automated Containment: [EDR Isolation/NAC Quarantine/None]
- Alert SLA: [Expected response time]

### Testing Results
| Test Date | Test Type | Canary Triggered | Alert Received | Containment Executed | Time to Alert |
|-----------|----------|-----------------|----------------|---------------------|---------------|