A professional AI-powered assistant designed to help security professionals plan, document, and report penetration testing engagements. This tool provides methodology guidance and documentation support, not attack automation.

This repository demonstrates:

• Professional penetration testing methodology knowledge
• AI integration for security assessment planning
• Structured documentation and reporting practices
• Industry-standard framework implementation (PTES, OWASP, NIST)
• Professional security consulting workflows

This is a methodology guidance and documentation tool. It helps security professionals structure their work professionally but does NOT:

• Automate exploitation or attacks
• Provide specific exploit code
• Replace skilled penetration testers
• Perform actual vulnerability scanning

AI-Penetration-Testing-Assistant/
├── agent-core/              # AI assistant core functionality
│   ├── pentest_assistant.py # Main AI assistant implementation
│   └── requirements.txt     # Python dependencies
├── methodology/             # Penetration testing methodology guides
│   ├── 01-pre-engagement-scoping.md
│   ├── 02-reconnaissance-information-gathering.md
│   ├── 03-vulnerability-identification.md
│   ├── 04-exploitation-planning.md
│   ├── 05-post-exploitation.md
│   └── 06-reporting.md
├── reconnaissance/          # Reconnaissance documentation tools
│   ├── reconnaissance-checklist.md
│   └── recon_organizer.py
├── reporting/              # Report generation tools
│   └── report_generator.py
├── templates/              # Professional document templates
│   ├── scope-of-work-template.md
│   ├── rules-of-engagement-template.md
│   ├── finding-template.md
│   └── report-template.md
├── scripts/                # Utility scripts
│   ├── cve_mapper.py      # CVE/CWE mapping
│   ├── prioritize_remediation.py
│   └── executive_summary.py
└── sample-outputs/         # Example outputs
    ├── sample-engagement-plan.md
    ├── sample-recon-summary.md
    └── sample-pentest-report.md

• Generate structured penetration testing plans
• Suggest relevant testing techniques based on target type
• Ask clarifying questions to refine engagement scope
• Provide methodology guidance
• Generate phase-specific documentation

Comprehensive guides covering:

• Pre-engagement and scoping
• Reconnaissance and information gathering
• Vulnerability identification
• Exploitation planning
• Post-exploitation considerations
• Professional reporting

• Structured reconnaissance checklist
• Finding documentation organizer
• Attack surface mapping support
• Service inventory management

• Professional report generation
• CVE/CWE mapping for findings
• CVSS score integration
• Remediation prioritization
• Executive summary generation

• Scope of Work documents
• Rules of Engagement
• Finding documentation
• Final report structure

• Python 3.8 or higher
• OpenAI API key

1. Clone this repository:

git clone https://github.com/Leegreen305/AI-Penetration-Testing-Assistant.git
cd AI-Penetration-Testing-Assistant

2. Install dependencies:

pip install -r agent-core/requirements.txt

3. Set up your OpenAI API key:

# Linux/Mac
export OPENAI_API_KEY='your-api-key-here'

# Windows Command Prompt
set OPENAI_API_KEY=your-api-key-here

# Windows PowerShell
$env:OPENAI_API_KEY="your-api-key-here"

Alternatively, create a .env file in the project root:

OPENAI_API_KEY=your-api-key-here

cd agent-core
python pentest_assistant.py

The assistant will:

1. Define engagement scope
2. Generate testing plan
3. Suggest relevant techniques
4. Provide methodology guidance

from pentest_assistant import PenTestAssistant

# Initialize assistant
assistant = PenTestAssistant()

# Define scope
target_info = {
    'target_name': 'Example Corp Web App',
    'target_type': 'web_application',
    'domains': ['example.com'],
    'ip_ranges': ['192.168.1.0/24'],
    'objectives': ['Identify security vulnerabilities']
}

scope = assistant.define_scope(target_info)

# Generate testing plan
plan = assistant.generate_testing_plan(scope)
print(f"Plan ID: {plan.plan_id}")
print(f"Methodology: {plan.methodology}")

# Get technique suggestions
techniques = assistant.suggest_techniques('web_application')
for technique in techniques:
    print(f"- {technique}")

cd reporting
python report_generator.py

Map findings to CVE/CWE identifiers:

cd scripts
python cve_mapper.py

Prioritize remediation:

python prioritize_remediation.py

Generate executive summary:

python executive_summary.py

This tool implements guidance from:

• Pre-engagement interactions
• Intelligence gathering
• Threat modeling
• Vulnerability analysis
• Exploitation
• Post-exploitation
• Reporting

• Information gathering
• Configuration and deployment management
• Identity management
• Authentication testing
• Authorization testing
• Session management
• Input validation
• Error handling
• Cryptography
• Business logic
• Client-side testing

• Planning phase
• Discovery phase
• Attack phase
• Reporting phase

The assistant provides specialized guidance for:

• Web Applications: OWASP Top 10, API security, authentication testing
• Network Infrastructure: Port scanning, service enumeration, network segmentation
• APIs: Authentication, authorization, rate limiting, data exposure
• Mobile Applications: Static/dynamic analysis, storage security, cryptography
• Cloud Infrastructure: IAM, storage security, network controls, container security

All generated documents follow professional standards:

• Executive summaries for business stakeholders
• Technical details for security teams
• CVSS v3.1 scoring
• CVE/CWE references
• Remediation recommendations with timelines
• Risk matrices and visual aids

This tool is designed for:

• Authorized security testing only
• Professional penetration testers and security consultants
• Educational purposes in controlled environments
• Security assessment planning and documentation

Do NOT use this tool for:

• Unauthorized access or testing
• Malicious purposes
• Attacking systems without permission
• Bypassing security controls illegally

Always obtain written authorization before conducting any security testing.

This repository showcases understanding of:

• Penetration testing methodologies and frameworks
• Security assessment planning and scoping
• Vulnerability classification and risk assessment
• Professional security documentation and reporting
• AI integration for security workflows
• Python development for security tools
• Industry compliance standards (PCI DSS, HIPAA, SOC 2)
• CVSS scoring and CVE/CWE mapping
• Executive communication and technical writing

To learn more about penetration testing:

• PTES: http://www.pentest-standard.org/
• OWASP Testing Guide: https://owasp.org/www-project-web-security-testing-guide/
• NIST SP 800-115: https://csrc.nist.gov/publications/detail/sp/800-115/final
• MITRE ATT&CK: https://attack.mitre.org/
• CVE Database: https://cve.mitre.org/
• CWE Top 25: https://cwe.mitre.org/top25/

This project is for educational and professional use. Always follow ethical guidelines and legal requirements when conducting security testing.

This is a demonstration project. For professional penetration testing services, consult with certified security professionals.

For questions about professional penetration testing methodology, consult:

• SANS Institute: https://www.sans.org/
• Offensive Security: https://www.offensive-security.com/
• EC-Council: https://www.eccouncil.org/

This tool provides guidance and documentation support for authorized security testing. The creators are not responsible for misuse. Always obtain proper authorization and follow all applicable laws and regulations.