Specialized Attack Simulations

Insider Threat Wargames

  • May 9, 2025
  • 0

Sherlocked Security – Insider Threat Wargames

Simulating Malicious Insider Attacks to Test Security Defenses and Employee Vigilance in Real-World Scenarios

1. Statement of Work (SOW)

Service Name: Insider Threat Wargames
Client Type: Enterprises, High-Security Organizations, Financial Institutions, Tech Companies, Government Agencies
Service Model: Simulated Insider Attack Scenarios + Social Engineering + Privilege Escalation + Data Exfiltration
Compliance Coverage: SOC 2, ISO 27001, NIST SP 800-53, GDPR, HIPAA

Testing Areas:

  • Insider Threat Simulation (Disgruntled Employee, Accidental Insider, Malicious Insider)
  • Privilege Escalation Tactics
  • Data Exfiltration Techniques
  • Lateral Movement and Escaping Detection
  • Endpoint Security Bypass
  • Email and Social Engineering Tactics
  • Mitigation of Insider Threats through Behavioral Analytics and Monitoring

2. Our Approach

[Target Identification] → [Insider Threat Simulation Design] → [Scenario Execution (Tactics, Techniques, Procedures)] → [Privilege Escalation & Lateral Movement] → [Data Exfiltration and Evasion] → [Detection Monitoring] → [Post-Scenario Reporting & Recommendations]

3. Methodology

[Target Profile Creation] → [Insider Threat Scenario Development] → [Execution of Social Engineering and Lateral Movement] → [Data Exfiltration Simulation] → [Behavioral Monitoring and Detection Analysis] → [Post-Engagement Analysis and Report Generation]

4. Deliverables to the Client

  1. Insider Threat Simulation Report with Detailed Findings
  2. Privilege Escalation and Lateral Movement Pathways Identified
  3. Data Exfiltration Techniques and Outcomes
  4. Effectiveness of Insider Threat Detection Tools (Behavioral Analytics, SIEM)
  5. Security Gaps in Insider Threat Detection and Mitigation Strategies
  6. Recommended Enhancements for Insider Threat Mitigation
  7. Post-Scenario Awareness Training Material for Employees

5. What We Need from You (Client Requirements)

  • List of key insider threat personas (e.g., disgruntled employee, contractor, third-party vendor).
  • Access to internal systems (user accounts, endpoints, network logs, privileged access tools).
  • SIEM and behavioral analytics system information for monitoring.
  • NDA and scope confirmation for simulated attacks.
  • Target user roles and privileges to simulate insider access levels.
  • Pre-existing threat intelligence reports for baseline threat analysis.

6. Tools & Technology Stack

  • Social Engineering Tools: Phishing Email Generators (GoPhish), Evilginx, Malicious USB Tools (Rubber Ducky, BadUSB)
  • Privilege Escalation Tools: Mimikatz, PowerSploit, BloodHound
  • Data Exfiltration Tools: Netcat, exfiltration via Cloud Storage (Google Drive, Dropbox), Rclone
  • Endpoint Security & Detection: CrowdStrike, Carbon Black, OSQuery
  • SIEM Tools: Splunk, ELK Stack, LogRhythm
  • Behavioral Analytics: ObserveIT, Varonis, Sumo Logic

7. Engagement Lifecycle

1. Pre-Engagement Briefing & Target Profiling → 2. Insider Threat Scenario Design → 3. Execution of Social Engineering & Privilege Escalation → 4. Data Exfiltration Simulation → 5. Detection & Response Monitoring → 6. Post-Scenario Reporting & Recommendations → 7. Employee Awareness Training

8. Why Sherlocked Security?

Feature Sherlocked Advantage
Realistic Insider Threat Scenarios Simulate various types of insider threats (e.g., disgruntled, negligent, malicious).
Advanced Privilege Escalation Leverage tools like Mimikatz and BloodHound to gain unauthorized access.
Data Exfiltration Techniques Utilize advanced exfiltration techniques (e.g., encrypted channels, cloud storage).
Detection & Monitoring Evaluation Evaluate the effectiveness of your SIEM and behavioral analytics tools in detecting insider threats.
Post-Engagement Recommendations Provide detailed recommendations to close security gaps and mitigate risks.

9. Real-World Case Studies

Malicious Insider Data Exfiltration

Issue: A system administrator with privileged access began downloading sensitive company data onto external devices.
Impact: Exfiltrated financial documents, customer PII, and intellectual property.
Fix: Implemented DLP (Data Loss Prevention) controls, restricted external device usage, and increased behavioral analytics for abnormal activity.

Insider Privilege Escalation and Lateral Movement

Issue: A low-level employee exploited a vulnerability in the system to escalate privileges, gaining unauthorized access to critical resources.
Impact: The employee moved laterally across systems, accessing payroll and confidential HR files.
Fix: Hardened system configurations, reduced privilege levels, and added role-based access control (RBAC).

10. SOP – Standard Operating Procedure

  1. Target Profile Creation

    • Identify different personas of insiders (e.g., disgruntled employee, trusted contractor, temporary worker).
    • Assign appropriate levels of access and privilege for each persona based on their role in the organization.

  2. Insider Threat Scenario Development

    • Develop various insider threat scenarios, including:
      • Malicious Insider: A trusted employee who intentionally steals data or sabotages systems.
      • Accidental Insider: A well-meaning employee who unknowingly makes critical errors or mishandles data.
      • Negligent Insider: An employee who disregards security policies and exposes vulnerabilities.

  3. Social Engineering Execution

    • Simulate phishing emails, USB drop attacks, or physical access attempts to exploit weaknesses in employee awareness.
    • Test employee susceptibility to social engineering tactics such as impersonation and deception.

  4. Privilege Escalation & Lateral Movement

    • Attempt privilege escalation using tools like Mimikatz and PowerSploit to exploit system vulnerabilities.
    • Use BloodHound to identify potential lateral movement paths and escalate access.

  5. Data Exfiltration Simulation

    • Test data exfiltration methods, such as sending sensitive data to a cloud storage service or copying it to a USB device.
    • Evaluate the organization’s ability to detect and block unauthorized data transfers.

  6. Behavioral Monitoring & Detection

    • Monitor the organization’s SIEM and endpoint security tools for signs of malicious activity.
    • Evaluate if behavioral analytics systems can identify abnormal actions (e.g., unusual login times, large data transfers).

  7. Post-Engagement Reporting & Recommendations

    • Provide detailed findings on the success or failure of the insider threat simulation.
    • Offer recommendations for strengthening insider threat defenses (e.g., improved access controls, more frequent audits, better monitoring systems).

11. Insider Threat Wargames Checklist

1. Scenario Development

  • Create realistic personas with varied motives (e.g., malicious insider, accidental insider).
  • Develop a plan for each scenario, including potential exploits, target systems, and data types.
  • Identify the appropriate attack vectors (e.g., phishing, USB attacks, social engineering).

2. Social Engineering & Attack Vectors

  • Use GoPhish or similar platforms to simulate phishing campaigns targeting insider roles.
  • Drop malicious USB devices in strategic locations to test physical security controls.
  • Create realistic, highly-targeted spear-phishing emails that impersonate executives or trusted colleagues.

3. Privilege Escalation & Lateral Movement

  • Use tools like Mimikatz, BloodHound, and PowerSploit to escalate privileges.
  • Attempt lateral movement within the network by exploiting misconfigured access controls.
  • Identify weak spots in access control policies and permissions across systems.

4. Data Exfiltration Simulation

  • Use tools like Netcat, Rclone, or custom scripts to exfiltrate data.
  • Simulate data exfiltration via encrypted tunnels or cloud storage.
  • Attempt large-scale data transfers to test the organization’s DLP and monitoring systems.

5. Detection & Monitoring

  • Ensure all attacks are monitored in real-time using SIEM tools (e.g., Splunk, LogRhythm).
  • Evaluate if behavioral analytics platforms (e.g., ObserveIT, Sumo Logic) can detect anomalies.
  • Monitor for suspicious activity such as unauthorized data access or unusual login patterns.

6. Reporting & Recommendations

  • Document the results of each attack scenario, including success rates, detection rates, and user responses.
  • Offer actionable recommendations to address security gaps and improve incident detection capabilities.
  • Provide specific guidelines for improving insider threat mitigation practices.
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