/pentest-plan

description: NYDFS penetration testing and vulnerability assessment requirements

NYDFS Penetration Testing Plan

Comprehensive guidance for meeting 23 NYCRR 500.05 penetration testing and vulnerability assessment requirements.

Arguments

• `$1` - Testing type (required: pentest, vulnerability-assessment, both)
• `$2` - Scope (optional: internal, external, web-app, cloud, comprehensive)

Regulatory Requirement

**Section 500.05**: Penetration Testing and Vulnerability Assessments

"Based upon its Risk Assessment, each Covered Entity shall conduct:

• **Annual penetration testing** of Information Systems
• **Bi-annual (twice yearly) vulnerability assessments** of Information Systems

including system components, reasonably designed to detect, identify, and report any material weaknesses, deficiencies, or vulnerabilities"

**Key Requirements**:

• Risk-based approach
• Conducted by qualified personnel
• Remediation of critical vulnerabilities
• Documented findings and remediation
• Annual cadence for pen testing
• Semi-annual for vulnerability assessments

Penetration Testing (Annual)

What is Penetration Testing?

**Simulated Cyber Attack**:

• Authorized attempt to exploit systems
• Identify exploitable vulnerabilities
• Test security controls effectiveness
• Validate defense capabilities
• Measure detection and response

**Differs from Vulnerability Assessment**:

• Active exploitation (not just detection)
• Attempts to gain unauthorized access
• Tests impact and chaining of vulnerabilities
• Mimics real-world attacker tactics
• Deeper technical analysis

Penetration Testing Frequency

**Annual Requirement**:

• Minimum once per calendar year
• More frequent if risk profile changes
• After significant system changes
• Following security incidents
• Before annual certification (recommended)

**Timing Considerations**:

• Schedule Q1-Q3 for April certification
• Avoid busy business periods
• Allow remediation time
• Coordinate with change freeze periods
• Factor in holidays and vacation

Penetration Testing Scope

**Risk-Based Scoping**:

• Focus on systems with nonpublic information
• Internet-facing assets (high priority)
• Critical business systems
• Recent deployments
• Third-party integrations
• High-risk applications

**Scope Components**:

**1. External Penetration Test**:

• Internet-facing systems and applications
• Web applications
• Email servers
• VPN endpoints
• Exposed APIs
• Cloud infrastructure

**2. Internal Penetration Test**:

• Internal network segmentation
• Domain controller security
• Lateral movement capabilities
• Privilege escalation paths
• Internal applications
• Data access controls

**3. Application Penetration Test**:

• Web applications (customer-facing)
• Mobile applications
• APIs
• Third-party integrations
• Custom-developed software

**4. Cloud Penetration Test**:

• Cloud infrastructure (AWS, Azure, GCP)
• Cloud-native applications
• Container security
• Serverless functions
• Cloud access controls

**5. Social Engineering** (optional but recommended):

• Phishing campaigns
• Vishing (voice phishing)
• Physical security testing
• Tailgating
• Pretexting

**6. Wireless Testing** (if applicable):

• WiFi security (WPA2/WPA3)
• Rogue access point detection
• Guest network isolation
• Wireless segmentation

Penetration Testing Methodology

**Industry Standards**:

• **PTES** (Penetration Testing Execution Standard)
• **OWASP** Testing Guide (web applications)
• **NIST SP 800-115** (Technical Guide to Information Security Testing)
• **OSSTMM** (Open Source Security Testing Methodology Manual)
• **MITRE ATT&CK** Framework (tactics and techniques)

**Testing Phases**:

**1. Planning and Reconnaissance**:

• Define scope and objectives
• Gather intelligence (OSINT)
• Identify targets and entry points
• Rules of engagement

**2. Scanning and Enumeration**:

• Port scanning
• Service identification
• Network mapping
• Asset discovery

**3. Vulnerability Identification**:

• Automated scanning
• Manual testing
• Configuration review
• Weakness analysis

**4. Exploitation**:

• Attempt to exploit vulnerabilities
• Gain unauthorized access
• Privilege escalation
• Lateral movement

**5. Post-Exploitation**:

• Assess impact
• Identify sensitive data access
• Persistence mechanisms
• Evidence collection

**6. Reporting**:

• Executive summary
• Technical findings
• Risk ratings
• Remediation recommendations
• Evidence and proof-of-concepts

Qualified Personnel

**Internal vs. External**:

**External Penetration Testing Firm** (Recommended):

• Independent perspective
• Specialized expertise
• Latest tools and techniques
• Credibility with regulators
• Professional insurance

**Internal Security Team**:

• Organizational knowledge
• Cost-effective
• Flexible timing
• Continuous testing capability
• May lack independence

**Qualifications to Look For**:

• **Certifications**:
• OSCP (Offensive Security Certified Professional)
• GPEN (GIAC Penetration Tester)
• CEH (Certified Ethical Hacker)
• GWAPT (GIAC Web Application Penetration Tester)
• OSCE (Offensive Security Certified Expert)
• **Experience**:
• Financial services penetration testing
• Regulatory compliance testing
• Similar environment experience
• Strong references
• **Methodology**:
• Documented testing process
• Industry standard frameworks
• Comprehensive reporting

Penetration Test Deliverables

**Executive Summary**:

• High-level findings
• Risk overview
• Business impact
• Strategic recommendations
• Compliance statement

**Technical Report**:

• Detailed vulnerability findings
• Exploitation methodology
• Proof-of-concept evidence
• Step-by-step reproduction
• Technical remediation steps
• CVSS scores
• CWE/CVE references

**Remediation Roadmap**:

• Prioritized findings (Critical, High, Medium, Low)
• Remediation recommendations
• Estimated effort
• Dependencies
• Quick wins

**Re-Test Report** (after remediation):

• Validation of f