Penetration testing is a security assessment methodology designed to evaluate the security of computer systems, networks, or applications. The main objective of penetration testing is to identify and classify vulnerabilities and weaknesses in a system’s defenses before malicious hackers can exploit them. It should be noted that a penetration test can be both internal and external in nature.

Penetration testing involves simulating real-world attacks to uncover potential security flaws that could be exploited by attackers. It typically follows a systematic cyclical process that includes the following steps:

1. Planning and reconnaissance: The penetration tester gathers information about the target system or network, such as its architecture, operating systems, applications, and potential vulnerabilities.
2. Scanning: The tester uses various tools and techniques to scan the target system for open ports, services, and other potential entry points...

In the context of penetration testing, stakeholders refer to individuals or groups who have a vested interest in or are affected by the results and outcomes of the penetration test. They are typically individuals or entities within an organization that commission or are involved in the testing process, as well as those who may be responsible for implementing the recommended security measures.

Here are some examples of stakeholders in penetration testing:

• Clients/organizations: The client or organization requesting the penetration test is a primary stakeholder. They are interested in identifying and addressing security vulnerabilities within their systems, networks, or applications. They may include executives, management, or security teams within the organization.
• IT/security team: The internal IT or security team of the organization being tested is also a significant stakeholder. They are responsible for implementing security controls, addressing vulnerabilities...

The term ethical, legal, and regulatory requirements in the context of penetration testing refers to the principles, laws, regulations, and guidelines that govern the ethical conduct, legal boundaries, and compliance obligations of penetration testers during their assessment activities. We will look at each of them in more detail as follows:

• Ethical requirements: Ethical considerations are essential in penetration testing to ensure that the activities are conducted responsibly, without causing harm or damage to the systems being tested. Ethical requirements often include obtaining proper authorization from the target organization, respecting privacy and confidentiality, and adhering to professional codes of conduct and standards. Penetration testers must act in an ethical manner and prioritize the best interests of the client and stakeholders.
• Legal requirements: Penetration testers must operate within the boundaries of the law...

Managing and executing a penetration test is a critical process that requires careful planning, coordination, and technical expertise. A well-managed and properly executed penetration test can help organizations identify vulnerabilities, assess their security posture, and make informed decisions to strengthen their defenses. Here are the key steps involved in managing and executing a penetration test:

1. Define objectives: Begin by clearly defining the objectives of the penetration test. Identify the systems, networks, or applications to be tested and determine the scope and limitations of the engagement. Consider the goals, such as identifying vulnerabilities, testing specific controls, or assessing the effectiveness of incident response. The objectives should also define the rules of engagement under which the test will be conducted. It should be noted that prior to the state of any penetration test, written permission should be obtained...

The cyber kill chain, developed by Lockheed Martin, is a systematic model that outlines the stages of a cyber-attack from the initial reconnaissance to achieving the attacker’s objectives. It provides a structured framework for understanding the different steps an attacker may take during an intrusion, allowing organizations to improve their cybersecurity defenses. In a penetration test, the cyber kill chain is leveraged as a guiding principle to assess and enhance the security of an organization’s systems and networks. When using the cyber kill, it will also make use of the MITRE framework for a detailed description of the actions performed.

During a penetration test, ethical hackers, known as penetration testers or “white hat” hackers, simulate real-world cyber-attacks to identify vulnerabilities and weaknesses in an organization’s defenses. The cyber kill chain is employed as a methodology to replicate the steps that...

There are several standards and frameworks that relate to penetration testing:

• Penetration Testing Execution Standard (PTES): PTES is a comprehensive framework guiding the execution of penetration tests. It offers a structured approach encompassing pre-engagement, intelligence gathering, threat modeling, vulnerability analysis, exploitation, post-exploitation, and reporting phases. PTES emphasizes methodical testing, ensuring thorough examination of security measures. By delineating clear steps and methodologies, it facilitates consistent and effective penetration testing practices. Adhering to PTES helps organizations identify and mitigate vulnerabilities, enhancing their overall cybersecurity posture and resilience against malicious attacks
• NIST SP 800-115: The National Institute of Standards and Technology (NIST) Special Publication 800-115 provides guidelines for performing information security testing and penetration testing. It offers...

Analysis and reporting are critical components of the penetration testing process that follow the active testing phases. Once the penetration tester has completed the scanning, gaining access, and any other exploitation activities, they transition to the analysis and reporting phase. This phase focuses on organizing, interpreting, and documenting the findings and observations made during the assessment. Here are key aspects of the analysis and reporting phase in penetration testing:

1. Findings analysis: The penetration tester thoroughly reviews the data collected throughout the assessment, including vulnerability scan results, exploitation logs, and any other relevant information. They analyze the findings to understand the extent of the compromise, the impact on the target system, and the potential risks associated with the identified vulnerabilities. All vulnerabilities must be classified and prioritized. We can achieve this using the CVSS scoring system. The...

In this chapter, we defined and discussed the legal, ethical, and software skills required when performing a penetration test. We discussed the role that various stakeholders can play at each stage of a penetration test, along with the various stages that comprise a penetration test. We explored the stages in the technical execution of a penetration test using the cyber kill chain, as well as defining the roles that various standards and legal frameworks play.

The next chapter provides a short technical introduction to programming using PowerShell. This chapter is not intended to be an introduction to PowerShell from first principles, but rather to outline the various components of PowerShell that we will be making use of in the following chapters.