A Guide to Pen Testing Methodologies for Beginners

Explore the comprehensive SOP for Penetration or Pen Testing, detailing methodologies, benefits, Types, Life Cycle, Tools, and frameworks for evaluating organizational security. Understand different testing types, phases, and the importance of decision tree analysis in enhancing cybersecurity posture.

Pen Testing: Types, Life Cycle, and Tools

Penetration testing is a structured process used to identify and exploit vulnerabilities in computer systems, applications, and infrastructure. Tests are categorized based on the environment and follow a defined life cycle, utilizing specialized tools.

Types

Penetration tests are customized based on the system or environment being evaluated:

Test Type	Overview	Best Methodology	Use Case
Network	Focuses on infrastructure like firewalls, routers, and switches to find misconfigurations, open ports, and weak protocols in both internal and external networks.	Black or Grey Box	Evaluating corporate network security against internal and external threats.
Web Application	Examines the security of web-based applications, APIs, and inputs for vulnerabilities such as SQL injection, XSS, and authentication flaws.	White Box	Assessing the security of public-facing applications and platforms.
Wireless	Evaluates wireless networks (e.g., Wi-Fi protocols) for encryption weaknesses and rogue access points, identifying risks associated with wireless access.	Grey Box	Assessing the security of office or guest wireless networks.
Social Engineering	Simulates human-centric attacks (e.g., phishing, pretexting) to test employee awareness and exploit human behavior, not technical flaws.	Varies based on scope	Testing organizational resilience against phishing and insider threats.
Physical	Tests physical security controls by attempting unauthorized access to buildings or hardware, mimicking attackers trying to enter secure areas.	Black Box	Assessing on-site security measures and the effectiveness of access controls.

The Life Cycle

A systematic approach ensures comprehensive assessment through the following five main stages:

1. Planning and Reconnaissance:
   • Goal: Define the scope and objectives of the test.
   • Activity: Gather detailed information about the target system (e.g., IP addresses, domain names) using both passive and active reconnaissance techniques.
2. Scanning:
   • Goal: Identify potential entry points and vulnerabilities.
   • Activity: Use techniques like port scanning, network mapping, and vulnerability scanning to detect open services, ports, and weaknesses. This is crucial for guiding further investigation.
3. Gaining Access:
   • Goal: Exploit identified vulnerabilities to breach the system.
   • Activity: Employ methods such as SQL injection, password cracking, or exploiting software flaws to obtain unauthorized access, demonstrating the potential impact of a successful attack.
4. Maintaining Access:
   • Goal: Establish a persistent presence in the system.
   • Activity: Install backdoors or other persistent tools to ensure continued access, simulating real-world attackers who remain undetected for prolonged periods.
5. Analysis and Reporting:
   • Goal: Document and communicate findings and recommended remediations.
   • Activity: Analyze the test results and create a detailed report describing discovered vulnerabilities, exploitation methods, and advice for corrective action. This stage provides a clear plan for security enhancement.

Key Pen Testing Tools

Specialized tools enable testers to perform tasks efficiently across the life cycle stages:

Tool	Description	Primary Use Stage
Nmap (Network Mapper)	A robust, open-source tool for network discovery, identifying live hosts, open ports, and running services.	Planning & Reconnaissance
Metasploit	A popular open-source framework offering a variety of exploits to simulate real-world attacks and assess system security.	Gaining Access
Burp Suite	An integrated platform for comprehensive web application security testing, including scanning, crawling, and exploiting common web vulnerabilities (e.g., SQL injection, XSS).	Scanning and Exploitation
Wireshark	A network protocol analyzer used to monitor and analyze network traffic in real-time, aiding in detecting suspicious activity and diagnosing network issues.	Analysis
John the Ripper	A widely used password cracking tool that supports various encryption techniques to identify weak passwords and confirm the effectiveness of password policies.	Gaining Access
OWASP ZAP (Zed Attack Proxy)	An open-source web application security scanner featuring a user-friendly interface and tools for detecting and manually testing security flaws in web applications.	Scanning

Standard Operating Procedure for Pen Testing

Penetration testing methodologies are crucial for an organization to evaluate its operational security across various domains, including physical location, workflow, human security, physical security, wireless security, telecommunication security, data networks security, and compliance. Adopting specific methodologies is vital for identifying potential threats and vulnerabilities within the environment. This document outlines the key penetration testing methodologies and the steps required for a comprehensive security assessment.

This report further analyzes penetration testing methodologies and defines its purpose: to identify security vulnerabilities in computing systems, detailing the Standard Operating Procedure (SOP) for pen testing and the concept of a decision-making tree.

Benefits of Pen Testing Methodologies

Penetration testing has become a significant component of security evaluation, enhancing the overall security of an organization’s systems and networks. The primary objective is to improve network security by attempting to compromise systems using techniques similar to those employed by malicious attackers.

Penetration testing is essential for the Information Technology infrastructure, particularly concerning the organization’s electronic assets. Its purpose is to identify and exploit vulnerabilities to bypass or defeat the security features of system components.

Types of Pen Testing Methodologies

Vulnerabilities can be found across various applications, such as web applications. Three main types of Pen Testing are commonly utilized:

• Black Box Pen Testing: Simulates a real-world cyberattack where the tester has no prior knowledge of the corporate IT infrastructure or the internal workings of the target web application (e.g., no access to source code or software architecture). This method can be time-consuming, often relying on automated processes to uncover weaknesses and vulnerabilities.
• White Box Pen Testing: Also known as Clear Box Testing, the tester is given full knowledge of and access to both the source code and software architecture of the web application. This approach is significantly faster than Black Box testing and allows for a much more thorough security assessment.
• Gray Box Pen Testing: A hybrid approach combining elements of both Black Box and White Box testing. The penetration tester has only partial knowledge of the internal workings of the web application, often restricted to specific access like software code or system architecture diagrams. Both manual and automated testing processes can used. The tester typically focuses efforts on the areas they know most about to find and exploit weaknesses or vulnerabilities.

Standard Operating Procedure (SOP) and Penetration Methods

The Standard Operating Procedure (SOP) a set of written instructions that document routine or repetitive activities to followed by an organization. Developing and using SOPs are integral to a successful quality system, ensuring individuals have the necessary information to perform their jobs correctly, thereby maintaining consistency in the quality and integrity of products or results. The SOP’s role is to ensure consistent quality, address safety concerns, and minimize miscommunication.

Pen Testing Methods

In addition to the three main types (Black, White, Gray Box), penetration testing can categorized by the perspective and knowledge shared:

• External Testing: Targets the company’s assets visible on the internet. Such as the web application, the company website, or email domain name servers (DNS). The goal is to gain access and extract valuable data.
• Internal Testing: The tester has access to an application behind a firewall, simulating an attack by a malicious insider. A common scenario is an attack resulting from an employee’s credentials being stolen via a phishing attack.
• Blind Testing: The tester is only given the name of the target organization. This provides security personnel with a real-time perspective of how an actual application assault would unfold.
• Double Blind Testing: Security personnel are unaware of the simulated attack beforehand. This mirrors a real-world breach attempt, preventing them from shoring up defenses ahead of time.
• Targeted Testing: The security personnel and the tester work together, keeping each other informed of their movements. This is a valuable training exercise, offering the security team real-time feedback from the attacker’s viewpoint.

The Core Phases of Pen Testing (Based on PTES)

Penetration testing simulates an attacker’s methods to circumvent security controls and gain access to an organization’s systems, moving beyond simple scanner results and automated tools. The Pen Testing Execution Standard (PTES) redefines the penetration test, providing a standardized framework adopted by leading security professionals. The PTES is divided into seven categories, each requiring a different level of effort depending on the target organization:

1. Pre-engagement Interactions: This initial phase involves discussing the scope, goals, and terms of the penetration test with the client. It is crucial to clearly communicate the engagement’s objectives, restrictions, and what a thorough, full-scope test entails.
2. Intelligence Gathering: The process of collecting information about the target organization using various methods, such as social media, Google hacking, and footprinting. A key skill for a tester is to learn about the target’s behavior, operations, and potential attack vectors. This stage includes identifying existing protection mechanisms and initial system probing.
3. Threat Modeling: Using the information gathered, the tester identifies existing vulnerabilities. Threat modeling determines the most effective attack methods, the type of information sought, and how the organization might compromised. It involves analyzing the organization from an adversary’s perspective to exploit weaknesses.
4. Vulnerability Analysis: Once the most viable attack method identified, the tester determines how to gain access to the target. This phase combines information from prior steps, incorporating port and vulnerability scans, banner grabbing data, and intelligence gathering to assess viable attack options.
5. Exploitation: Often considered the most exciting part, this should done with precision rather than brute force. Exploits should only launched when there is high confidence in their success. Blindly launching a mass onslaught of exploits is unproductive, noisy, and provides little value to the client.

Other thing

1. Post Exploitation: A critical component where the tester differentiates themselves from a casual hacker. The goal is to provide value by identifying critical infrastructure, key systems, and the data most valued by the company and demonstrate attacks that would have the greatest business impact after initial access gained.
2. Reporting: The most vital element of the penetration test. The information compiled is essential for the organization’s information security program and for preventing future attacks. The report should go beyond a technical list of vulnerabilities, offering recommendations on how the organization can use the findings to raise awareness, remediate issues, and improve overall security. For example, for SQL injection vulnerabilities, recommendations might include sanitizing all user input, leveraging parameterized SQL queries, running SQL with limited user accounts, and turning on custom error messages.

Decision Tree Analysis for Pen Testing

You will briefly describe what a decision tree for Pen Testing is, citing at least one or two sources. For instance: According to Smith (2011) and Richards (2014), a pen testing decision tree is a diagrammatic model used to map out potential security risks and attack paths, helping a tester decide on the most effective strategy.

Subsequently, you will describe various attack trees with examples, and select one, providing the rationale for your choice. Incorporate three additional references here.

The chosen attack tree will placed in the appendix. You may also propose an adaptation of this attack tree based on a specific scenario; while not mandatory, attempting an adaptation can earn extra credit. The evaluation will focus on common sense and effort rather than technical perfection.