All About Penetration Testing

Contents

• What is Pentesting?
• Pentesting Approaches
• Types of Pentesting
• Phases of Pentesting
• Common Tools Used in Pentesting
• Why is Pentesting Important?
• Penetration Testing Frameworks
  • OSSTMM (Open Source Security Testing Methodology Manual)
  • PTES (Penetration Testing Execution Standard)
  • NIST SP 800-115 (Technical Guide to Information Security Testing and Assessment)
  • OWASP Testing Guide
  • ISSAF (Information Systems Security Assessment Framework)
  • The Cyber Kill Chain (Lockheed Martin)
  • MITRE ATT&CK Framework
  • Summary of Frameworks
  • Which Framework to Choose?
• Conclusion

What is Pentesting?

Pentesting, or penetration testing, is the process of simulating cyberattacks on computer systems, networks, or web applications to identify security vulnerabilities that malicious hackers could exploit. The primary goal of pentesting is to enhance the overall security posture of the target by uncovering weaknesses before they can be exploited in real-world attacks.

Pentesting Approaches

• White Box: The tester is given full access to internal information such as source code, architecture diagrams, and credentials, allowing for a comprehensive analysis of security vulnerabilities.
• Black Box: The tester has no prior knowledge of the system and simulates an external attacker with no internal access, focusing on discovering vulnerabilities from an outsider’s perspective.
• Gray Box: The tester has partial knowledge of the system, such as limited credentials or some internal details, providing a balanced view of both external and internal threats.

Types of Pentesting

• Web Application Pentesting: Web apps are common targets for attackers due to their exposure to the internet. Web App Pentesting focuses on identifying security issues such as: Cross-Site Scripting (XSS), SQL Injection, Authentication flaws, Security misconfigurations, Cross-Site Request Forgery (CSRF), Server-Side Request Forgery (SSRF), Remote Code Execution (RCE), etc.
• Network Pentesting: Network pentesting involves assessing the security of internal or external networks, identifying misconfigurations, or vulnerabilities such as: Open ports, Weak encryption protocols, Firewall bypass, Unauthorized access points, etc.
• Mobile Application Pentesting: With the increasing use of mobile apps, pentesting for Android and iOS platforms helps secure the apps from vulnerabilities such as insecure data storage, improper session handling, and insecure communications.
• API Pentesting: APIs (Application Programming Interfaces) are increasingly targeted by attackers. API Pentesting ensures secure communication between services by testing for weaknesses like: Broken authentication, Insecure API endpoints, Improper error handling, etc.
• Red Team Engagements: Unlike regular pentesting, Red Teaming simulates full-blown attacks on an organization’s security infrastructure, involving multiple attack vectors to test not only the systems but also the responsiveness of the security teams.
• Cloud Pentesting: With the widespread adoption of cloud computing, Cloud Pentesting focuses on identifying vulnerabilities in cloud infrastructure such as insecure configurations, weak access controls, and data exposure in services like AWS, Azure, or GCP.
• Wireless Pentesting: Wireless networks can expose an organization to attacks if not properly secured. Wireless Pentesting involves assessing the security of Wi-Fi networks, testing for vulnerabilities such as weak encryption protocols (e.g., WPA2), rogue access points, and unauthorized devices.
• Social Engineering: Social engineering tests the human element of security by simulating phishing attacks, impersonation, or other psychological techniques to trick individuals into revealing sensitive information or performing actions that compromise security.
• Build and Configuration Review: This type of pentesting involves reviewing the security configurations of systems, applications, and infrastructure to identify misconfigurations, outdated software, or insecure settings that could lead to vulnerabilities.
• Physical Pentesting: Physical security is often overlooked. This type of pentesting assesses physical access controls, such as locks, security cameras, and restricted access areas, to ensure that unauthorized personnel cannot gain entry to sensitive locations.

Phases of Pentesting

• Reconnaissance: In this phase, pentesters gather as much information as possible about the target through open-source intelligence (OSINT), network scanning, and identifying public-facing assets.
• Scanning and Enumeration: This phase involves using tools to actively scan the target for open ports, services, and potential vulnerabilities.
• Exploitation: Exploiting the identified vulnerabilities to see if they can lead to unauthorized access or other malicious actions.
• Post-Exploitation: After gaining access, pentesters evaluate the extent of potential damage by attempting to escalate privileges or extract sensitive information.
• Reporting: A comprehensive report is generated, detailing the vulnerabilities found, the impact of exploitation, and the recommended steps to mitigate or fix the issues.

Common Tools Used in Pentesting

• Burp Suite: A comprehensive tool for web app pentesting, used for intercepting and manipulating traffic, scanning for vulnerabilities, and automating tests.
• Nmap: A network scanner used for discovering hosts, services, and open ports in a network.
• Metasploit: An exploitation framework that provides a wide range of payloads for vulnerability testing.
• OWASP ZAP: A free, open-source tool focused on finding vulnerabilities in web applications.
• Wireshark: A packet analyzer used for network traffic analysis and troubleshooting.

Why is Pentesting Important?

• Proactive Security: Regular pentesting helps identify and fix vulnerabilities before they can be exploited by attackers.
• Compliance: Many industries have strict regulations (e.g., GDPR, PCI-DSS) that require regular security testing to protect sensitive data.
• Risk Reduction: By identifying weaknesses, organizations can prioritize the remediation of critical vulnerabilities, reducing the risk of breaches.
• Reputation: Ensuring that systems are secure helps maintain the trust of clients and customers, avoiding the reputational damage that can follow a data breach.

Penetration Testing Frameworks

A list of commonly used penetration testing frameworks and their methodologies for conducting security assessments.

1. OSSTMM (Open Source Security Testing Methodology Manual)

• Overview:
  OSSTMM is a comprehensive framework covering various security testing aspects, including networks, applications, and physical security. It emphasizes objective-based testing and measurement.

• Key Areas:
  • Information Security
  • Vulnerability Assessment
  • Controls Testing
  • Process and Methodology
• Use Case: Best for organizations that need a structured approach for auditing security systems.

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2. PTES (Penetration Testing Execution Standard)

• Overview:
  PTES is a standardized methodology covering all phases of penetration testing, from pre-engagement to post-engagement tasks.

• Phases of PTES:
  1. Pre-engagement Interactions
  2. Intelligence Gathering
  3. Threat Modeling
  4. Vulnerability Analysis
  5. Exploitation
  6. Post-Exploitation
  7. Reporting
• Use Case: Suitable for both beginners and advanced pentesters.

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3. NIST SP 800-115 (Technical Guide to Information Security Testing and Assessment)

• Overview:
  Published by NIST, this framework focuses on methodologies for testing information systems.

• Key Areas:
  • Planning
  • Discovery
  • Attack and Exploit
  • Post-Exploit
  • Reporting
• Use Case: Commonly used in organizations seeking compliance with industry standards.

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4. OWASP Testing Guide

• Overview:
  OWASP provides a methodology for web application pentesting with its Testing Guide.

• Phases in OWASP Testing Guide:
  1. Information Gathering
  2. Configuration and Deployment Management Testing
  3. Identity Management Testing
  4. Authorization Testing
  5. Session Management Testing
  6. Input Validation Testing
  7. Error Handling Testing
  8. Reporting
• Use Case: Ideal for web application security assessments.

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5. ISSAF (Information Systems Security Assessment Framework)

• Overview:
  ISSAF provides a step-by-step methodology for information security assessments.

• Phases of ISSAF:
  1. Pre-engagement
  2. Information Gathering
  3. Assessment and Testing
  4. Post-Assessment
• Use Case: Best for complex organizational environments.

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6. The Cyber Kill Chain (Lockheed Martin)

• Overview:
  The Cyber Kill Chain is designed to track the stages of a cyber attack.

• Phases of Cyber Kill Chain:
  1. Reconnaissance
  2. Weaponization
  3. Delivery
  4. Exploitation
  5. Installation
  6. Command and Control (C2)
  7. Actions on Objectives
• Use Case: Useful for understanding real-world attack phases and structuring a red-team pentest.

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7. MITRE ATT&CK Framework

• Overview:
  MITRE ATT&CK is a knowledge base of adversarial tactics and techniques.

• Key Areas:
  • Tactics: What the adversary wants to achieve (e.g., initial access, persistence).
  • Techniques: How the adversary achieves their goals (e.g., phishing, brute-force attacks).
• Use Case: Best for red teaming and simulating sophisticated attacks.

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Summary of Frameworks

Framework	Focus Area	Best For
OSSTMM	Broad security testing (network, physical)	Comprehensive, detailed assessments
PTES	Full pentesting methodology	Standardized approach to all penetration tests
NIST SP 800-115	Information system testing	Compliance-driven environments (government, enterprise)
OWASP Testing Guide	Web application security	Web application penetration testing
ISSAF	Information security assessment	Large organizations, enterprises
Cyber Kill Chain	Attack behavior modeling	Simulating real-world attacks
MITRE ATT&CK	Adversarial tactics and techniques	Red teaming and advanced threat simulations

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Which Framework to Choose?

• For Web Application Testing: Use the OWASP Testing Guide.
• For Comprehensive Pentests: Use PTES or OSSTMM.
• For Compliance: Use NIST SP 800-115.
• For Red Teaming: Use MITRE ATT&CK or Cyber Kill Chain.

These frameworks ensure your penetration tests are methodical, consistent, and thorough.

Conclusion

Pentesting is a critical component of any organization’s cybersecurity strategy. By simulating real-world attacks, pentesters help secure systems, protect data, and maintain the integrity of digital infrastructures. Whether it’s a web application, network, or mobile app, regular pentesting ensures that security weaknesses are identified and addressed before they can cause harm.