How Are Penetration Tests Conducted?

by | Jul 7, 2023 | Penetration Testing

Penetration testing, or pen testing for short, is critical to any comprehensive cybersecurity strategy. Pen testing involves simulating an attack on an organization’s network, applications, or systems to identify vulnerabilities that a malicious actor could exploit. This article will examine how penetration tests are conducted, including the different types of tests and the methodologies used to conduct them.

Types of Penetration Tests

There are several types of penetration tests, and the type chosen depends on the scope and objectives of the test. Some of the most common types of pen tests include:

  1. External Network Penetration Testing: An external network penetration test is a security assessment that aims to evaluate the security posture of an organization’s external-facing network assets. This test aims to identify vulnerabilities and weaknesses that an attacker could exploit to gain unauthorized access to sensitive information or systems. External network penetration testing typically involves a simulated attack on an organization’s internet-facing systems, such as web applications, email servers, and remote access services.
  2. Internal Network Penetration Testing: An internal network penetration test is a type of assessment that involves testing the security controls of an organization’s internal network. This test aims to identify vulnerabilities and potential attack vectors that an attacker could exploit to gain unauthorized access to the network. The internal network penetration test is typically carried out from the perspective of an insider threat or an attacker who has already gained access to the internal network.
  3. Web Application Penetration Testing: A web application penetration test is a type of testing that focuses specifically on the security of web applications. This testing involves using various techniques to identify vulnerabilities in the web application that attackers could exploit. A web application penetration test aims to identify any security weaknesses in the application, such as SQL injection or cross-site scripting, and to provide recommendations for improving the application’s security.
  4. Social Engineering (Phishing): A social engineering penetration test involves attempting to trick employees or other individuals within an organization into revealing sensitive information, clicking on malicious links, or taking other actions that could compromise the organization’s security. This type of test typically involves phishing emails or other forms of communication that appear to come from a trusted source, such as an internal IT department or a legitimate vendor.
  5. Physical Social Engineering: A physical social engineering penetration test evaluates an organization’s physical security controls by simulating a real-world scenario where an attacker attempts to gain unauthorized access to sensitive areas or information through social engineering techniques. The goal is to identify weaknesses in an organization’s physical security controls, such as access control systems, security policies, procedures, employee awareness, and compliance.
  6. IoT Penetration Testing: An IoT (Internet of Things) penetration test involves assessing the security of IoT devices, including smart home appliances, industrial control systems, and medical devices. IoT devices are becoming increasingly popular and can be found in many households and businesses. However, due to their limited processing power and memory, IoT devices often have vulnerabilities that hackers can exploit.
  7. Wireless Penetration Testing: A wireless penetration test, also known as a wireless security assessment, is a type of penetration test that focuses on the security of wireless networks. This type of test is particularly important for organizations that rely on wireless networks to transmit sensitive data, such as financial or healthcare information. A wireless penetration test typically involves a team of ethical hackers using specialized tools to identify vulnerabilities in wireless networks, such as weak passwords, unencrypted data transmissions, or unauthorized access points.
  8. Mobile Application Penetration Testing: A mobile application penetration test identifies vulnerabilities in mobile applications running on different operating systems, including iOS and Android. Mobile application penetration testing is crucial because mobile devices are increasingly becoming a primary means of accessing the internet and storing sensitive data. Mobile application penetration tests help to identify vulnerabilities in the application’s logic, data storage, and communication channels between the application and the server.
  9. Red Team Assessment: A red team assessment, also known as red teaming, is a comprehensive and sophisticated form of penetration testing that goes beyond identifying vulnerabilities and weaknesses in an organization’s defenses. Red teaming aims to simulate real-world attacks by mimicking the tactics, techniques, and procedures (TTPs) of actual attackers to test the effectiveness of an organization’s overall security posture.

Overall, the type of penetration test conducted will depend on the specific objectives and goals of the organization. It is important to select the appropriate type of test and methodology to ensure that the test results are relevant and useful for improving the organization’s security posture.

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Also, you will have a different result depending on the approach of penetration test you choose, each with its own pros and cons. The three main types/approaches of pen testing are black box, gray box, and white box. The choice of penetration testing approach depends on the specific goals of the test, the budget, and the resources available. While black box testing provides the most realistic simulation of a cyber attack, it can be time-consuming and expensive. White box testing provides the most comprehensive coverage of the system, but it can be the most costly method. Gray box testing provides a good balance between the two but may not identify all vulnerabilities.

  1. Black Box Penetration Testing:

In black box testing, the tester has no prior knowledge of the system being tested. This method tries to simulate an attack by an outsider without internal knowledge of the system.


  • Provides a realistic simulation of an actual cyber attack
  • Tests the overall security posture of the system
  • Helps to identify vulnerabilities that other methods may miss


  • Can be time-consuming and expensive
  • May not identify all vulnerabilities
  • Can disrupt normal system operations

  1. Gray Box Penetration Testing:

In gray box testing, the tester has limited knowledge of the system being tested. This method tries to simulate an attack by a user with some understanding of the system’s internal workings.


  • Helps to identify vulnerabilities that may not be apparent from the outside
  • Simulates a more realistic attack scenario
  • Provides better coverage than black box testing


  • Can be more expensive than black box testing
  • May not identify all vulnerabilities
  • Can disrupt normal system operations

  1. White Box Penetration Testing:

In white box testing, the tester has complete knowledge of the system being tested. This method tries to simulate an attack by an insider with full access to the system.


  • Provides the most comprehensive coverage of the system
  • Can identify vulnerabilities that other methods may miss
  • Can be less disruptive to normal system operations


  • Can be the most expensive method
  • May not provide a realistic simulation of an actual cyber attack
  • May not identify vulnerabilities that only occur in a live environment

Methodologies Used in Penetration Testing

There are several methodologies used in penetration testing, including:

  1. Open-Source Security Testing Methodology Manual (OSSTMM): The methodology consists of guidelines, procedures, and best practices for testing the security of an organization’s systems, networks, and applications. It covers various topics, including information gathering, vulnerability scanning, exploitation, password cracking, social engineering, wireless security, physical security, and more. The OSSTMM is designed to be technology-agnostic, meaning it can be applied to any environment, regardless of the technology used.
  2. Penetration Testing Execution Standard (PTES): This methodology is similar to the OSSTMM but includes additional phases, such as scoping and reconnaissance. The PTES framework provides a structured approach to identifying and exploiting vulnerabilities in an organization’s systems, applications, and infrastructure. The PTES framework comprises seven phases: pre-engagement, intelligence gathering, threat modeling, vulnerability analysis, exploitation, post-exploitation, and reporting.
  3. Information Systems Security Assessment Framework (ISSAF): The Information Systems Security Assessment Framework (ISSAF) is a comprehensive and systematic approach to information security assessment. It is a free and open-source framework that guides security professionals and organizations on planning, designing, and implementing practical security assessments. The ISSAF is designed to be flexible and adaptable to different environments, technologies, and threat landscapes. This methodology is based on a seven-step process that includes planning, reconnaissance, discovery, enumeration, vulnerability mapping, exploitation, and post-exploitation.
  4. National Institute of Standards and Technology (NIST) Cybersecurity Framework: The National Institute of Standards and Technology (NIST) Cybersecurity Framework is a set of guidelines for organizations to manage and reduce cybersecurity risks. The framework was created in response to Executive Order 13636, which called for developing a voluntary framework to improve the cybersecurity of critical infrastructure. The framework consists of three parts: the Core, Implementation Tiers, and Framework Profiles.
  5. NIST 800-115: NIST 800-115 is a technical guide that guides the implementation of the Federal Information Security Management Act (FISMA) by outlining the steps and procedures for conducting a comprehensive security assessment of an organization’s information system. The guide is specifically designed for federal agencies but can also be used by non-government organizations.

The Penetration Testing Process

The Penetration Testing Process

How are penetration tests conducted? Regardless of the methodology used, the penetration testing process generally follows the same steps:

  1. Planning and Scoping

The first step in a penetration test is planning and scoping. This involves identifying the goals and objectives of the test, as well as the scope of the test. The scope should include the systems and networks to be tested and any specific vulnerabilities or areas of concern. The goals and objectives should be clearly defined and communicated to all stakeholders, including the client, the testers, and any third-party vendors or contractors involved in the test.

During the planning and scoping phase, the testers will gather as much information as possible about the target systems and networks. This may involve conducting reconnaissance and intelligence gathering activities, such as scanning the target networks for open ports and services, identifying potential attack vectors, and mapping out the network topology. The testers may also review any available documentation, such as network diagrams, system architecture diagrams, and security policies and procedures.

  1. Vulnerability Assessment

Once the scope has been defined and the target systems and networks have been identified, the next step is to conduct a vulnerability assessment. This involves scanning the target systems and networks for known vulnerabilities and weaknesses. The testers may use various tools and techniques to conduct this assessment, including vulnerability scanners, port scanners, and network mapping tools.

During the vulnerability assessment phase, the testers will identify potential vulnerabilities attackers could exploit. This may include outdated software, misconfigured systems, weak passwords, or unpatched systems. The testers will then prioritize the identified vulnerabilities based on their potential impact on the target systems and networks.

  1. Exploitation

Once the vulnerabilities have been identified and prioritized, the testers will attempt to exploit them. This may involve using known exploits and attack techniques or developing custom exploits tailored to the target systems and networks. The exploitation phase aims to gain access to the target systems and networks and escalate privileges to gain further access.

The testers may use various techniques to exploit the identified vulnerabilities, including social engineering, phishing attacks, and network-based attacks. These attacks may be targeted at specific individuals or systems or be more general.

  1. Post-Exploitation

Once the testers have gained access to the target systems and networks, the next step is maintaining access and escalating privileges. This involves establishing persistent access to the target systems and networks and ensuring that the access remains undetected.

During the post-exploitation phase, the testers may install backdoors, establish command and control channels, and exfiltrate sensitive data from the target systems and networks. They may also attempt to move laterally through the network, searching for other systems to compromise and additional data to exfiltrate.

  1. Reporting

The final step in a penetration test is reporting. This involves documenting the test findings, including any identified vulnerabilities, the methods used to exploit them, and the potential impact of these vulnerabilities on the target systems and networks. The report should also include recommendations for mitigating the identified vulnerabilities and improving the overall security posture of the target systems and networks.

The report should be written in clear and concise language that is understandable to technical and non-technical stakeholders. It should also include detailed technical information for those responsible for implementing the recommended mitigations and improvements.

In conclusion, penetration testing is essential for ensuring the security of an organization’s network, systems, and applications. Penetration testers use many tools and techniques to simulate real-world attacks and identify vulnerabilities attackers could exploit. By conducting penetration tests, organizations can better understand their security posture and make informed decisions about their security investments.

Penetration testing involves various phases, including reconnaissance, scanning, enumeration, exploitation, and post-exploitation. Each phase requires careful planning and execution to ensure that the penetration testing team achieves its objectives while minimizing the risk of causing damage or disruption to the target systems.

When asking yourself how are penetration tests conducted, it is essential to have a team of skilled and experienced professionals with a deep understanding of various operating systems, networks, and applications. Moreover, they must possess excellent communication and reporting skills to ensure the test results are clearly communicated to the organization’s management and stakeholders.

Finally, it is worth noting that penetration testing is not a one-time process but an ongoing effort to ensure that an organization’s security posture remains strong over time. Regularly scheduled penetration tests can help organizations stay on top of emerging threats and vulnerabilities and take proactive measures to mitigate them.

The importance of conducting penetration testing cannot be overstated. It is a critical process that can help organizations identify vulnerabilities and improve their security posture. While the process can be complex and time-consuming, the benefits of a successful penetration test far outweigh the effort required to conduct it. With the right team and tools in place, organizations can remain secure and protected against even the most sophisticated attacks. Artifice security is a trusted and reliable pentesting partner for companies serious about protecting their assets and data from cyber threats. Their expertise, comprehensive testing approach, customized methodology, actionable results, and expertise make them an excellent choice for any company looking to improve its security posture.

Want a consultation for your next penetration test? Book a call with Artifice Security today.

Artifice Security is a top provider of cybersecurity solutions, offering exceptional penetration testing services. Below are some compelling reasons why companies should consider hiring us to perform their pen tests:

  1. Expert Penetration Testers: Our team comprises highly skilled and knowledgeable testers who understand the most recent threats and attack techniques. Working with clients across diverse industries gives them a comprehensive view of security challenges and solutions.
  2. Extensive Testing: At Artifice Security, we adopt a comprehensive pen testing methodology that covers all aspects of a company’s security posture. Our testers use both automated and manual testing techniques to identify vulnerabilities and gauge the security controls’ overall effectiveness.
  3. Customized Testing Approach: We take a tailored approach to our pen testing, where we customize the scope and depth of the test to meet each client’s specific needs. We work collaboratively with the client to comprehend their goals and objectives and then develop a testing plan to achieve them.
  4. Actionable Results: We provide detailed and actionable reports presenting identified vulnerabilities and recommendations for remediation. Our reports are designed to be understood easily by both technical and non-technical stakeholders, providing clear guidance on enhancing the organization’s security posture.
  5. Compliance: Our pen testing services comply with various regulatory requirements, including PCI DSS, HIPAA, and GDPR. Companies can guarantee compliance with the necessary regulations and avoid potential fines and legal issues by hiring us to perform a pen test. Artifice Security is a reliable and trusted partner for companies that prioritize protecting their assets and data from cyber threats. Our team’s expertise, comprehensive testing approach, customized methodology, actionable results, and experience make us an exceptional choice for any company seeking to enhance its security posture.

Artifice Security is a trusted and reliable partner for companies committed to safeguarding their assets and data from cyber threats. With their experience, comprehensive testing approach, customized methodology, actionable results, and expertise, Artifice Security is an excellent choice for any company looking to bolster its security posture.

To learn more about penetration testing services, approaches, costs, and more, visit our Ultimate Guide to Penetration Testing page.

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