Penetration Testing Cheat Sheet

Updated 2026-05-25

Penetration testing is a structured security assessment process that simulates real-world cyberattacks to identify vulnerabilities before malicious actors can exploit them. Operating within legal authorization and ethical frameworks, penetration testers use reconnaissance, scanning, exploitation, post-exploitation, and reporting phases to validate security controls across networks, web applications, cloud environments, and endpoints. The practice has expanded significantly with cloud infrastructure, containerized workloads, API-driven architectures, and AI systems, requiring testers to master not only traditional network exploitation but also modern cloud-native and LLM-specific attack surfaces. Understanding the difference between vulnerability scanning and actual exploitation is crucial — pentesting validates real-world impact, confirms exploitability, and demonstrates how an attacker could chain multiple weaknesses to achieve objectives like data exfiltration or privilege escalation.

What This Cheat Sheet Covers

This topic spans 20 focused tables and 223 indexed concepts. Below is a complete table-by-table outline of this topic, spanning foundational concepts through advanced details.

Table 1: Penetration Testing MethodologiesTable 2: Testing Approaches and ScopesTable 3: Reconnaissance TechniquesTable 4: Scanning and EnumerationTable 5: Exploitation TechniquesTable 6: Post-Exploitation and PersistenceTable 7: Web Application Vulnerabilities (OWASP Top 10)Table 8: Password AttacksTable 9: Cloud and Container Penetration TestingTable 10: API Security TestingTable 11: Mobile Application Security TestingTable 12: Wireless and Network AttacksTable 13: Social Engineering TechniquesTable 14: Penetration Testing ToolsTable 15: Rules of Engagement and Legal ConsiderationsTable 16: Reporting and RemediationTable 17: AI and LLM Security TestingTable 18: Defense Evasion TechniquesTable 19: CI/CD and Supply Chain Security TestingTable 20: IoT and Hardware Penetration Testing

Table 1: Penetration Testing Methodologies

Established frameworks give structure to what would otherwise be an ad-hoc process, ensuring consistent coverage and defensible methodology when findings are reviewed by clients or auditors. Choosing the right framework — or combining elements of several — shapes the entire engagement from scoping to final report.

Framework	Example	Description
PTES (Penetration Testing Execution Standard)	Seven phases: Pre-engagement → Intelligence Gathering → Threat Modeling → Vulnerability Analysis → Exploitation → Post-Exploitation → Reporting	Community-driven standard defining a comprehensive penetration testing workflow with technical guidelines for each phase.
OWASP Testing Guide	Web application-specific methodology covering authentication, session management, input validation, business logic flaws	• Focused on web application security • provides detailed testing procedures for each OWASP Top 10 vulnerability type
MITRE ATT&CK Framework	Tactics: Initial Access → Execution → Persistence → Privilege Escalation → Defense Evasion → Credential Access → Discovery → Lateral Movement → Exfiltration → Impact	• Knowledge base of real-world adversary tactics and techniques • use to structure threat-informed tests and red team operations; v19 (April 2026) added Stealth and Defense Impairment tactics.
NIST SP 800-115	Technical Guide to Information Security Testing and Assessment; covers network, application, and wireless testing	U.S. government standard providing comprehensive guidance on planning, conducting, and reporting security assessments.

Table 1: Penetration Testing Methodologies

Framework	Example	Description
PTES (Penetration Testing Execution Standard)	Seven phases: Pre-engagement → Intelligence Gathering → Threat Modeling → Vulnerability Analysis → Exploitation → Post-Exploitation → Reporting	Community-driven standard defining a comprehensive penetration testing workflow with technical guidelines for each phase.
OWASP Testing Guide	Web application-specific methodology covering authentication, session management, input validation, business logic flaws	• Focused on web application security • provides detailed testing procedures for each OWASP Top 10 vulnerability type
MITRE ATT&CK Framework	Tactics: Initial Access → Execution → Persistence → Privilege Escalation → Defense Evasion → Credential Access → Discovery → Lateral Movement → Exfiltration → Impact	• Knowledge base of real-world adversary tactics and techniques • use to structure threat-informed tests and red team operations; v19 (April 2026) added Stealth and Defense Impairment tactics.
NIST SP 800-115	Technical Guide to Information Security Testing and Assessment; covers network, application, and wireless testing	U.S. government standard providing comprehensive guidance on planning, conducting, and reporting security assessments.