Sherlocked Security – Insider Threat Simulation
Test and Mitigate Risks from Malicious or Negligent Insiders in Your Organization
1. Statement of Work (SOW)
Service Name: Insider Threat Simulation
Client Type: Enterprises, Financial Institutions, Healthcare, Government Agencies
Service Model: Simulation of Insider Threat Scenarios Using Ethical Hacking Techniques
Compliance Coverage: NIST 800-53, SOC 2, ISO 27001, HIPAA
Simulation Types:
- Malicious Insider Attack Simulation
- Negligent Insider Simulation
- Elevated Privilege Abuse
- Data Exfiltration via Insider
- Insider Fraud & Financial Manipulation
- Insider Attack via Remote Access Tools
- Insider Collaboration with External Threats
2. Our Approach
[Pre-engagement & Scope Agreement] → [Insider Threat Modeling] → [Simulated Insider Attacks] → [Privilege Escalation Testing] → [Data Exfiltration Simulation] → [Behavioral Analytics Testing] → [Detection & Response Evaluation] → [Results Mapping & Reporting] → [Retesting & Validation]
3. Methodology
[Kickoff & Scope Agreement] → [Insider Threat Profiling] → [Simulate Insider Attack Scenarios] → [Privilege Escalation & Lateral Movement] → [Test Data Exfiltration & Collusion] → [Assess Detection & Response Systems] → [Final Report & Remediation]
4. Deliverables to the Client
- Insider Threat Simulation Report: Comprehensive overview of insider attack simulations and test results
- Privilege Escalation Findings: Detailed mapping of privilege escalation vectors and their exploitation
- Data Exfiltration Report: Findings related to the exfiltration of sensitive data by simulated insiders
- Behavioral Analytics Evaluation: Assessment of how well insider activity is detected by monitoring tools
- Executive Summary: High-level report for executives on the insider threat landscape and organizational risks
- Remediation Recommendations: Best practices and action items for mitigating insider threats
- Retesting & Certification: Validation of improvements and re-testing post-remediation
5. What We Need from You (Client Requirements)
- A list of key personnel with privileged access
- Logs and telemetry data from endpoint security and network monitoring tools
- Access to user behavior analytics and any threat detection tools in use
- Collaboration with HR, legal, and IT teams to model realistic insider threats
- Information on any previous incidents or ongoing insider threat programs
- Access to training and awareness programs for employees on insider threats
- Permission to test with minimal disruption to operations (ideally in a staging environment)
6. Tools & Technology Stack
- Custom Tools / Scripts for simulating insider threat attacks
- Cobalt Strike for post-exploitation and privilege escalation
- Empire for PowerShell-based attack simulations
- Metasploit Framework for exploiting vulnerabilities and escalating privileges
- Burp Suite for testing web applications in insider scenarios
- BloodHound for mapping Active Directory privileges and lateral movement
- PowerShell Empire for executing PowerShell-based attack commands
- Pupy for advanced RAT-based insider attack simulations
- Wireshark for network traffic analysis during data exfiltration attempts
- Nexpose for scanning internal network systems and identifying vulnerable assets
7. Engagement Lifecycle
1. Discovery Call → 2. Scope Definition & Strategy → 3. Insider Threat Profiling → 4. Attack Simulation (Insider Threat Scenarios) → 5. Privilege Escalation & Data Exfiltration Testing → 6. Detection & Response Testing → 7. Draft Report → 8. Final Report & Remediation Recommendations → 9. Retesting & Certification
8. Why Sherlocked Security?
| Feature | Sherlocked Advantage |
|---|---|
| Comprehensive Insider Threat Modeling | Realistic simulation of both malicious and negligent insider threats |
| Privilege Escalation Testing | Simulate and identify potential privilege escalation paths |
| Data Exfiltration Scenarios | Test for insider data exfiltration over various channels |
| Custom Tools & Scripts for Simulation | Tailored tools for testing insider attack scenarios in depth |
| Behavioral Analytics Testing | Evaluate how well your monitoring systems detect insider threats |
| Remediation & Retesting | Comprehensive remediation recommendations and post-fix validation |
9. Real-World Case Studies
Insider Threat in a Financial Institution
Client: Global Investment Bank
Scenario: A disgruntled employee attempts to exfiltrate sensitive financial data and manipulate trade data.
Findings: Privilege escalation vulnerabilities allowed the insider to bypass controls.
Fix: Improved access control and monitoring of critical financial systems. Enhanced user behavior analytics to detect anomalies.
Insider Threat in Healthcare Organization
Client: National Healthcare Provider
Scenario: A negligent insider accidentally shared sensitive patient data outside the organization.
Findings: Weak data access policies and insufficient training on handling patient data led to the incident.
Fix: Strengthened access control policies and implemented mandatory data protection training for employees.
10. SOP – Standard Operating Procedure
- Discovery call and scope definition
- Insider threat profiling and scenario development
- Simulate insider threats using different techniques (malicious, negligent, etc.)
- Perform privilege escalation and lateral movement testing
- Test data exfiltration via various channels
- Evaluate monitoring and detection capabilities for insider activities
- Draft report and conduct review call with key stakeholders
- Final report delivery with remediation recommendations
- Retesting post-remediation and certification
11. Insider Threat Simulation Checklist
1. Insider Threat Modeling
- Identify key personnel with privileged access
- Develop profiles of potential insider threats (malicious, negligent, and unintentional)
- Review historical insider threat incidents for patterns and lessons learned
2. Privilege Escalation & Lateral Movement Testing
- Test privilege escalation techniques within Active Directory environments (T1071, T1105)
- Evaluate lateral movement through internal networks and systems (T1021)
- Simulate abuse of admin privileges (T1071)
3. Data Exfiltration Testing
- Test data exfiltration methods via email, USB, and cloud storage (T1041)
- Simulate covert data exfiltration using encrypted or hidden channels (T1071)
- Test for data exfiltration over network protocols such as FTP, HTTP, and DNS (T1041)
4. Insider Fraud & Financial Manipulation
- Simulate fraudulent activities such as unauthorized transactions (T1071, T1105)
- Test for abuse of internal financial systems for personal gain (T1071)
5. Detection & Monitoring Testing
- Evaluate how well endpoint detection systems identify suspicious insider behavior (T1071)
- Test network monitoring systems for detecting exfiltration and privilege escalation (T1071)
- Review user behavior analytics and their ability to flag anomalous insider actions (T1071)