Penetration testing, also known as pen testing or pentest, is a crucial aspect of cyber security testing. It involves simulating an attack on a computer system or network to identify vulnerabilities and evaluate the effectiveness of security controls. The process of penetration testing is essential for organizations looking to improve their overall security posture and reduce the risk of a security breach.
This article provides a comprehensive guide to the steps involved in a penetration test, including planning and preparation, information gathering, threat modeling, vulnerability scanning, exploitation, post-exploitation, and reporting. The guide highlights the benefits and risks associated with each stage and includes information about various tools and techniques used in each stage, such as the Metasploit framework and the Comptia Pentest+ certification.
Whether you’re looking to perform a pen test in-house or to hire a professional penetration testing company, this guide will provide you with the information you need to understand the process and make informed decisions about your security posture.
1. Planning and Preparation
Planning and preparation is the first stage of a penetration test. It sets the foundation for the entire testing process, determining the scope of the test, the goals, and objectives. The tester must have a clear understanding of the target system, including its architecture and technologies used. In this stage, the tester and the organization agree on the scope of the test and the objectives to be achieved.
The scope of the test refers to the systems, applications, and infrastructure that will be tested. The scope should be clearly defined and agreed upon by both the tester and the organization. This helps to ensure that the test is focused and efficient, and that the results are meaningful and relevant to the organization. The scope should also be flexible enough to allow the tester to adjust their approach as they gain a deeper understanding of the target system.
The goals and objectives of the test are also defined in this stage. These may include identifying and exploiting vulnerabilities, evaluating the effectiveness of security controls, or testing the organization’s incident response plan. The goals and objectives should be specific, measurable, and relevant to the organization. They should also align with the organization’s overall security objectives and risk management strategy.
Once the scope and goals of the test have been defined, the tester must have a clear understanding of the target system, including its architecture and technologies used. This involves researching and gathering information about the target system, including the operating systems, applications, and network infrastructure. The tester should also have a good understanding of the organization’s security policies and procedures, as well as any regulatory or compliance requirements that may apply.
It’s also important to understand the target system’s users, including their roles and responsibilities, access controls, and authentication mechanisms. This can help the tester identify potential attack vectors and prioritize their testing efforts.
In addition to understanding the target system, the tester must also have a good understanding of the testing environment. This includes the tools and techniques that will be used during the test, as well as any limitations or restrictions that may apply. For example, the tester may need to work within specific time constraints or may be prohibited from using certain tools or techniques.
Once the scope, goals, and objectives of the test have been defined, and the tester has a good understanding of the target system and testing environment, the next step is to plan the testing process. This involves developing a testing methodology, identifying potential attack vectors, and determining the testing schedule. The testing methodology should be tailored to the specific requirements of the organization and the target system, and should be flexible enough to allow the tester to adjust their approach as they gain a deeper understanding of the target system.
Finally, it’s important to establish clear lines of communication between the tester and the organization. This includes establishing a point of contact within the organization who can provide information and support during the test, as well as a clear understanding of the reporting process and format.
The tools and frameworks commonly used in this stage include:
- OSSTMM (Open Source Security Testing Methodology Manual) – A comprehensive methodology for conducting security testing
- Microsoft Threat Modeling Tool – A tool for visualizing, analyzing, and documenting the security of software systems
2. Information Gathering
Information gathering is the second stage of a penetration test. In this stage, the tester collects as much information as possible about the target system and its environment. This information is used to identify potential attack vectors and to develop a more comprehensive understanding of the target system.
The first step in the information gathering stage is reconnaissance. Reconnaissance refers to the process of researching the target organization, its employees, and its public-facing web presence. This information can be used to identify potential attack vectors and to develop a more comprehensive understanding of the target system.
One of the most effective ways to gather information about the target organization is through open-source intelligence (OSINT) techniques. OSINT involves using publicly available information to gather intelligence about an organization, its employees, and its systems. This information can be found on the organization’s website, social media accounts, and other public sources.
The tester should also gather information about the target system’s infrastructure, including its network topology, IP addresses, and domain names. This information can be obtained through a variety of methods, including network mapping, whois queries, and DNS reconnaissance. The tester should also gather information about the target system’s technologies, including the operating systems, applications, and network devices in use.
Another important component of the information gathering stage is social engineering. Social engineering is the process of tricking individuals into revealing sensitive information. This can be accomplished through a variety of methods, including phishing, baiting, and pretexting. Social engineering can provide valuable information about the target system and its users, including login credentials, access controls, and security policies.
Once the tester has gathered as much information as possible about the target system and its environment, the next step is to analyze the information and identify potential attack vectors. This includes identifying vulnerabilities in the target system, such as unpatched software, weak passwords, and misconfigured security controls. The tester should also identify potential entry points into the target system, such as open ports, unprotected web applications, and weak authentication mechanisms.
Some of the tools and frameworks used in this phase include:
- Nmap – A network exploration and security auditing tool
- Whois – A tool for querying information about domain names and IP addresses
- Google Dorks – A technique for using Google to search for sensitive information
- Maltego – A tool for information gathering and threat intelligence analysis
3. Threat Modelling
Threat modeling is the process of identifying potential attack vectors and weaknesses in a target system. It involves analyzing the information gathered in the previous stage of a penetration test to identify the most significant risks to the system. The goal of threat modeling is to provide a systematic and comprehensive approach to security risk management, allowing organizations to prioritize their efforts and allocate resources where they are most needed.
The first step in the threat modeling process is to create a representation of the target system. This can be in the form of a diagram, a flowchart, or a table. The representation should include all the components of the system, such as applications, databases, networks, and users. The representation should also include the relationships between the components, such as the flow of data and the relationships between users and systems.
Next, the tester should identify potential threats to the system. This can be done by examining the components of the system and the relationships between them, as well as by considering the motivations of potential attackers. Threats can come from a variety of sources, including external attackers, internal users, and system errors.
Once the potential threats have been identified, the tester should prioritize them based on their likelihood and impact. This can be done using a variety of methods, including a risk matrix or a threat scorecard. The goal is to focus on the most significant risks to the system, and to allocate resources where they are most needed.
The tester should then evaluate the existing security controls in place to mitigate the identified threats. This can include analyzing the strength of passwords, the configuration of firewalls, and the effectiveness of intrusion detection systems. The tester should also consider the potential impact of the threats and the likelihood of successful exploitation.
Once the existing security controls have been evaluated, the tester should identify any gaps or weaknesses in the security posture of the system. This includes identifying any vulnerabilities in the system, such as unpatched software, weak passwords, and misconfigured security controls. The tester should also identify any entry points into the system, such as open ports, unprotected web applications, and weak authentication mechanisms.
The final step in the threat modeling process is to develop recommendations for remediation. This includes identifying the most effective ways to mitigate the identified threats, such as patching vulnerabilities, strengthening passwords, and configuring security controls more effectively. The recommendations should be prioritized based on their likelihood and impact, and should align with the organization’s overall security objectives and risk management strategy.
Some of the tools and frameworks used in this phase are:
- Microsoft Threat Modeling Tool – A tool for visualizing, analyzing, and documenting the security of software systems
- STRIDE (Spoofing, Tampering, Repudiation, Information Disclosure, Denial of Service, and Elevation of Privilege) – A framework for identifying and categorizing security threats
- PASTA (Process for Attack Simulation and Threat Analysis) – A framework for conducting threat modeling and attack simulation
4. Vulnerability Scanning
Vulnerability scanning is the process of using automated tools to identify known vulnerabilities in a target system. It is an important component of a penetration test, providing a starting point for the tester to focus their efforts on the most promising attack vectors. Vulnerability scanning can be a time-saving and efficient way to identify potential security weaknesses, allowing the tester to prioritize their testing efforts and allocate resources where they are most needed.
Vulnerability scanning tools work by using a database of known vulnerabilities and exploiting techniques to identify weaknesses in the target system. The tools typically scan the target system for open ports and services, and then use this information to identify potential vulnerabilities. The tools can also perform tests for common misconfigurations, such as weak passwords and unpatched software, and can provide a detailed report of the results.
Vulnerability scanning tools can be used to scan a wide range of systems, including networks, web applications, and individual computers. The tools can also be used to scan a range of protocols, including TCP, UDP, and HTTP. The results of the scan can be used to identify potential attack vectors, such as unpatched software, weak passwords, and misconfigured security controls.
One of the benefits of vulnerability scanning is its speed and efficiency. Automated tools can scan a target system much faster than a manual assessment, allowing the tester to quickly identify potential security weaknesses. The tools can also be configured to scan the target system on a regular basis, providing ongoing visibility into the security posture of the system.
Another benefit of vulnerability scanning is its ability to identify known vulnerabilities. The tools use a database of known vulnerabilities and exploiting techniques, allowing them to quickly identify potential weaknesses in the target system. This information can be used to prioritize the testing efforts and allocate resources where they are most needed.
It’s important to note, however, that vulnerability scanning tools can only identify known vulnerabilities. The tools rely on the availability of information about a vulnerability in their database, and may not be able to identify new or unknown vulnerabilities. This is why it’s important to also perform manual testing, in addition to vulnerability scanning, to provide a more comprehensive assessment of the target system’s security posture.
Vulnerability scanning can also produce false positive results, meaning that the tool identifies a potential vulnerability that does not actually exist. This can occur for a variety of reasons, including misconfigured tools, false information in the vulnerability database, or limitations of the scanning tool. It’s important to validate the results of the scan, using manual testing and other methods, to ensure that the results are accurate and meaningful.
Some of the tools and frameworks used in this phase are:
- Nessus – A vulnerability scanner for identifying and reporting on vulnerabilities in a target system
- OpenVAS – An open-source vulnerability scanning and management tool
- Core Impact – A commercial vulnerability scanner and penetration testing tool
- Qualys – A cloud-based vulnerability scanning and management platform
5. Exploitation
Exploitation is the process of using vulnerabilities to gain unauthorized access and control over a target system. It is a crucial component of a penetration test, allowing the tester to evaluate the effectiveness of security controls and identify areas for improvement. Exploitation can involve bypassing security controls, such as firewalls, intrusion detection systems, and access controls, to gain access to sensitive information or to gain control over the target system.
The exploitation stage of a penetration test begins with identifying potential vulnerabilities in the target system. This can be done through a variety of methods, including vulnerability scanning, manual testing, and threat modeling. Once potential vulnerabilities have been identified, the tester then attempts to exploit them to gain access and control over the target system.
Exploitation can involve a range of techniques, including exploiting software vulnerabilities, exploiting misconfigured systems, and social engineering. Software vulnerabilities can include unpatched software, buffer overflows, and SQL injection, among others. Misconfigured systems can include weak passwords, open ports, and misconfigured firewalls, among others. Social engineering can involve tricking individuals into revealing sensitive information, such as login credentials.
Once the tester has gained access to the target system, they will then attempt to escalate their privileges. This can involve attempting to gain administrative access, bypassing security controls, or exploiting misconfigurations. The goal of escalation is to gain greater access and control over the target system, allowing the tester to access sensitive information or to cause harm to the system.
One of the key challenges in the exploitation stage of a penetration test is avoiding detection. The tester must be careful not to cause damage to the system or to disrupt normal operations, as this can negatively impact the organization and undermine the goals of the test. The tester must also be careful to avoid detection by security controls, such as firewalls, intrusion detection systems, and antivirus software.
Some of the tools and frameworks used in this phase are:
- Metasploit Framework – An open-source framework for developing, testing, and executing exploits
- Core Impact – A commercial vulnerability scanner and penetration testing tool
- Metasploit Termux – A version of the Metasploit Framework for the Termux mobile application on Android
6. Post-exploitation
Post-exploitation is the process of maintaining access and escalating privileges within a target system after successfully exploiting a vulnerability. It is an important component of a penetration test, allowing the tester to evaluate the effectiveness of security controls and identify areas for improvement. The goal of post-exploitation is to demonstrate the potential impact of a successful attack, and to provide recommendations for remediation.
Once the tester has successfully exploited a vulnerability, they will attempt to maintain access to the target system. This can involve installing backdoors, creating persistent access points, or hiding their presence on the system. The goal of maintaining access is to ensure that the tester can return to the target system at a later time, even if the initial vulnerability has been closed or the system has been rebooted.
The tester will then attempt to escalate their privileges within the target system. This can involve attempting to gain administrative access, bypassing security controls, or exploiting misconfigurations. The goal of escalation is to gain greater access and control over the target system, allowing the tester to access sensitive information or to cause harm to the system.
Once the tester has gained access and escalated their privileges, they will then attempt to gather sensitive information from the target system. This can include usernames, passwords, financial information, and confidential business information, among others. The goal of gathering information is to demonstrate the potential impact of a successful attack, and to provide recommendations for remediation.
In addition to gathering information, the tester may also attempt to cause harm to the target system. This can include deleting files, modifying data, or disrupting normal operations. The goal of causing harm is to demonstrate the potential impact of a successful attack, and to provide recommendations for remediation.
Some of the tools and frameworks used in this phase are:
- Metasploit Framework – An open-source framework for developing, testing, and executing exploits
- Meterpreter – A powerful and versatile payload included in the Metasploit Framework
7. Reporting
The final stage of a penetration test is to document the findings and present a report to the organization. The report provides the organization with a clear understanding of the vulnerabilities discovered and the potential impact of a successful attack. The report should be comprehensive, easy to understand, and provide actionable recommendations for remediation.
The first step in the reporting stage is to gather and organize all the data collected during the penetration test. This includes information about the target system, the vulnerabilities discovered, the methods used to exploit them, and any sensitive information gathered during post-exploitation. The data should be organized in a logical and concise manner, making it easy for the reader to understand the results of the test.
Next, the tester should provide a detailed description of the vulnerabilities discovered. This should include information about the severity of the vulnerability, the potential impact of a successful attack, and the methods used to exploit the vulnerability. The description should also include screenshots and other relevant information to provide a clear understanding of the vulnerability and its potential impact.
The report should also include a description of the methods used to exploit the vulnerabilities. This should include information about the tools and techniques used, as well as a step-by-step explanation of the exploitation process. The description should be detailed and comprehensive, allowing the reader to understand the methods used to exploit the vulnerabilities and the potential impact of a successful attack.
The most important component of the report is the recommendations for remediation. This should include specific and actionable recommendations for improving the security posture of the target system, based on the vulnerabilities discovered during the test. The recommendations should be prioritized based on their severity and potential impact, allowing the organization to address the most critical vulnerabilities first.
The recommendations should also include information about best practices and industry standards, to help the organization improve their overall security posture. This can include information about password policies, firewall configuration, and software patching, among others. The recommendations should be clear and concise, making it easy for the organization to understand and implement the recommendations.
In addition to the technical recommendations, the report should also include a summary of the results of the test. This should include information about the scope of the test, the goals and objectives, and the overall results. The summary should be easy to understand, and should provide a clear picture of the security posture of the target system.
The report should also include a section on the limitations of the test. This should include information about any constraints or limitations that may have impacted the results of the test, such as a limited scope or limited access to the target system. The limitations section should be transparent and honest, allowing the reader to understand the limitations of the test and to make informed decisions based on the results.
Some common tools and frameworks used in this phase are:
- Microsoft Threat Modeling Tool – A tool for visualizing, analyzing, and documenting the security of software systems
- OpenVAS – An open-source vulnerability scanning and management tool
- Core Impact – A commercial vulnerability scanner and penetration testing tool
The Takeaway
Penetration testing is an essential aspect of cyber security testing that involves simulating an attack on a computer system or network to identify vulnerabilities and evaluate the effectiveness of security controls. This comprehensive guide outlined the steps involved in a penetration test, including planning and preparation, information gathering, threat modeling, vulnerability scanning, exploitation, post-exploitation, and reporting.
Each stage of the penetration test involves using specific tools and techniques to achieve its goals. Tools and frameworks commonly used in each stage include Nmap, Metasploit Framework, Core Impact, OpenVAS, and Microsoft Threat Modeling Tool.
By understanding the steps involved in a penetration test, organizations can make informed decisions about their security posture and take the necessary steps to improve their overall security. Whether you’re looking to perform a pen test in-house or to hire a professional penetration testing company, this guide provides you with the information you need to make informed decisions about your security posture.
