penetration-testing

name	penetration-testing
description	Use when planning or conducting authorized penetration tests against web applications, APIs, networks, and mobile apps. Covers pen testing methodologies (OWASP, PTES, OSSTMM), scoping and rules of engagement, tool selection, reporting, and remediation verification. USE FOR: penetration testing, pen test methodology, PTES, OSSTMM, OWASP Testing Guide, web app pen testing, API pen testing, network pen testing, mobile pen testing, vulnerability assessment, bug bounty, responsible disclosure, rules of engagement DO NOT USE FOR: automated security scanning in CI/CD (use security-testing), threat modeling before implementation (use threat-modeling), AI/LLM-specific adversarial testing (use ai-security or red-teaming)
license	MIT
metadata	{"displayName":"Penetration Testing","author":"Tyler-R-Kendrick"}
compatibility	claude, copilot, cursor
references	[{"title":"OWASP Web Security Testing Guide","url":"https://owasp.org/www-project-web-security-testing-guide/"},{"title":"Penetration Testing Execution Standard (PTES)","url":"http://www.pentest-standard.org"},{"title":"NIST SP 800-115 Technical Guide to Information Security Testing","url":"https://csrc.nist.gov/publications/detail/sp/800-115/final"}]

Penetration Testing

Overview

Penetration testing is the authorized practice of simulating attacks against a system to discover exploitable vulnerabilities before malicious actors do. Unlike automated security scanning (SAST/DAST), pen testing involves human expertise to chain vulnerabilities, test business logic flaws, and assess real-world exploitability. Pen tests are conducted under a clear scope and rules of engagement, and results are reported with severity ratings and remediation guidance.

Important: Penetration testing must always be performed with explicit written authorization. Unauthorized testing is illegal in virtually every jurisdiction. Ensure you have a signed rules of engagement document before beginning any testing.

Key References

Title	Author(s)	Focus
The Web Application Hacker's Handbook	Stuttard & Pinto	Web app vulnerability discovery and exploitation
Penetration Testing	Georgia Weidman	Hands-on pen testing methodology
The Hacker Playbook 3	Peter Kim	Red team tactics and techniques
OWASP Testing Guide v4.2	OWASP Foundation	Comprehensive web application testing methodology
PTES (Penetration Testing Execution Standard)	PTES.org	Industry-standard pen testing framework

Methodologies

Methodology	Scope	Phases	Best For
OWASP Testing Guide	Web applications	Information gathering, configuration testing, identity management, authentication, authorization, session management, input validation, error handling, cryptography, business logic, client-side	Web app and API pen tests
PTES	General	Pre-engagement, intelligence gathering, threat modeling, vulnerability analysis, exploitation, post-exploitation, reporting	Full-scope engagements
OSSTMM	Networks and systems	Scope, channel, index, vectors, verification, resolution	Network and infrastructure testing