Penetration tests are simulated cyberattacks executed by white hat hackers on systems and networks. These simulations aim to detect vulnerabilities, misconfigurations, errors, and other weaknesses that real attackers could exploit.
Pentesters work closely with the organization whose security posture they are hired to improve. However, different types of penetration tests, methodologies, and best practices must be followed for optimal results.
Different Methods and Types of Penetration Testing
When a company hires a penetration testing service, it typically chooses from three types of simulations: black, white, and gray box testing. These differ in the amounts of information provided to the pentester before running the simulated attacks.
- Black box pentest: Zero knowledge, or Black box, pentests are the most time-consuming and costly types of penetration tests. However, they are also the most realistic tests. They come very close to the steps that real attackers go through. Penetration testers are not given any information and must go in “blind.” They have to start by mapping the entire infrastructure to find weak entry points and identify where critical business assets are located.
- Gray box pentest: In gray box tests, also known as limited knowledge tests, the organization gives some information to the pentesters but does not fully disclose the architecture. The information provided to pentesters is usually an employer’s access credentials or knowledge of internal networks or applications.
- White box pentest: Organizations provide ethical hackers with information on their systems and simulation targets in white box penetration testing. The information provided can include application source code, user credentials, privileged administrative access, and other critical data, which can be used to simulate an internal attack. Since much of the access information is provided upfront, these tests are less expensive than black box tests.
Additionally, tests can be comprehensive or limited. Limited tests can focus on narrower targets such as networks, Internet of Things (IoT) devices, physical security, cloud security, web applications, or other system components.
Comprehensive & Limited Testing
Penetration tests can be comprehensive, where organizations test their entire network, systems, and endpoints, or limited to specific infrastructure components. Extensive tests are rare, expensive, and hard to execute.
Because organizations usually have penetration testing programs that outline and schedule tests periodically, tests tend to be limited to one or a few components. Limited tests allow for a deeper dive into a particular environment, are used for updates and new applications, are more focused, and are cheaper and faster to run.
Some limited penetration tests include:
- Network pentests: Testing is performed on all possible internal or external entry points to identify vulnerabilities.
- Wireless pentests: Wireless assessments evaluate the security of wireless networks and devices.
- Physical pentests: Penetration testers use various tools and techniques, including lockpicks, RFID cloners, and social engineering to gain access to a physical location.
- Web application pentests: Web application penetration tests consist of ethical hackers testing the security of web or software applications.
- Cloud pentests: Penetration testers assess the security of cloud environments, infrastructure, applications, and services.
- Mobile pentests: Like web application pentests, hackers test mobile applications for vulnerabilities.
- IoT pentests: Testing is performed on Internet of Things-connected devices and networks.
Also read: Penetration Testing vs. Vulnerability Testing: An Important Difference
Depending on the size of the target, a penetration test can be performed by a single ethical hacker, However, they can also involve multiple teams actively working to attack or defend the target.
Red & Blue Teams
In all three types of pentests, security teams and penetration testers occasionally engage in what is known as a red team vs. blue team strategy.
Pentesters, posing as red teams, focus on using offensive capabilities to attack their target network or applications, while blue teams focus on detecting and defending their assets from the attackers. This strategy allows security teams to learn what actual attacks look like and measure their response and performance.
- Red Team: Red teams are typically smaller groups of ethical hackers, locksmiths, programmers, and social engineers. These members are tasked with using a variety of tactics to mimic a real-world attacker attempting to breach a network or application and report their findings.
- Blue Team: Blue teams protect an organization’s systems and networks from cyberattacks. This can include maintaining the networks and devices, handling user access, and addressing vulnerabilities and security issues. Blue teams may consist of several teams like network security, endpoint security, or the security operations center (SOC).
Recently, security teams have implemented a purple team strategy that consists of members from both red and blue teams working together to actively determine attack and defense strategies that go beyond individual pentests to include comprehensive, ongoing testing objectives for optimal effectiveness.
No matter what team or strategy you prefer, companies and their IT and security teams must determine a penetration testing program that satisfies their needs. This is crucial for organizations looking to protect their assets from all possible threats.
Read this article for more information on the differences between red, blue, and purple teams.
Starting a Pentesting Program
Most organizations hire outside companies to conduct penetration testing engagements, while larger companies with larger security teams could start their own internal program. The added benefit of having an internal penetration testing team is that they can carry out continuous and more comprehensive testing programs.
Whether you hire an outside company or start an internal team, knowing the penetration testing process is best. This will help you design your pentesting program to ensure your goals are met and the most critical assets remain protected.
For more on pentesting program design and assembling a team, read How to Implement a Penetration Testing Program in 10 Steps.
6 Steps of Penetration Testing
Companies hiring penetration services should also familiarize themselves with each assessment phase. Ethical hackers must know intimately about all steps, including the first and final steps, which are often left out. The phases of penetration tests are:
- Pre-engagement: This phase is when penetration testers and the clients determine the scope of the assessment, rules of engagement, approved tools and techniques, and other procedures.
- Reconnaissance & Information Gathering: This part of the assessment involves testers collecting as much information as possible about their target. This information is essential as it will be used in future phases of the penetration test.
- Scanning & Analysis: In the scanning and analysis phase, penetration testers use tools and other methods to identify and verify vulnerabilities and weaknesses in a network, application, or device.
- Exploitation: The exploitation phase is when the penetration testers exploit the information and vulnerabilities found in previous phases to gain access to their target.
- Post Exploitation: This phase occurs after successful exploitation, where the testers gain further information and access to the target system, attempt to elevate privileges, and move, or “pivot,” to other parts of the network.
- Reporting & Post Assessment: After the penetration test is done, testers must write and deliver a report to their clients that explains the entire process, vulnerabilities found, exploitation tools and techniques used, and the level of access gained. Additionally, penetration testers will recommend how to fix and remediate the vulnerabilities discovered during the assessment and improve the security posture.
Although the phases of a penetration test stay the same, the methodology may differ depending on which one you follow.
Read our article, “Penetration Testing Phases & Steps Explained” to learn more about the penetration testing lifecycle.
Penetration Testing Methodologies
Leading organizations have developed their own penetration testing methodologies that serve as a blueprint for ethical hackers. These methodologies provide clear direction on how pentests are conducted. However, methodologies can vary depending on the business or organization’s needs. For example, some methods meet national security and federal standards, while others are focused on private companies.
Some of these organizations include the PTES, OSSTMM, NIST, and OWASP:
- NIST: Developed by the National Institute of Science and Technology, NIST Special Publication 800-115, Technical Guide to Information Security Testing and Assessment is the most specific from start to finish. Companies that want to meet high-security standards adopt this methodology for penetration testing. NIST is also mandatory for several businesses and organizations.
- OSSTMM: Developed by the Institute for Security and Open Methodologies (ISECOM), the Open Source Security Testing Methodology Manual (OSSTMM) is a popular pentest methodology. It is also specific, allowing white hat hackers to customize their tests to an organization’s particular demands. The widely used OSSTMM sets recognized test standards, is peer-reviewed, and is based on a scientific approach.
- OWASP: The Open Web Application Security Project, or OWASP, designed its methodology for web and mobile applications, IoT devices, and application programming interfaces (APIs). It can help penetration testers and is used in the early stages of app development. Additionally, the methodology is updated to help the security community stay on top of the latest technologies.
- PTES: The Penetration Testing Execution Standard (PTES) framework offers guidance on all stages of a pentest. It consists of seven main sections. These cover everything testers need: initial communications, intelligence gathering, threat modeling phases, vulnerability research, exploitation, and post-exploitation. In addition, PTES developed a comprehensive and detailed technical guide for each phase.
- Compliance Testing: Organizations like the Department of Health and Human Services and the PCI Standards Council have also published pentesting guidance for organizations seeking to comply with HIPAA and PCI-DSS standards.
Knowing the proper methodology for an assessment will be important for the penetration tester and the organization being tested. In addition, knowing the tools of the trade is equally important.
Check out this article about penetration testing frameworks, including some of our top picks.
Top Pentesting Tools
There are several penetration test tools in the market; some are free to use, while others are commercial solutions. Some of the most popular and effective solutions pentesters use include Kali Linux, Burp Suite, Wireshark, and John the Ripper:
- Kali Linux: Kali Linux is an open-source operating system maintained by Offensive Security that facilitates penetration testing, security forensics, and other activities. Kali Linux is an all-in-one system that includes 600 open-source security tools.
- Burp Suite: Burp Suite is a suite of application security testing tools developed by PortSwigger with free and paid license options. It also includes the popular Burp Proxy, which allows penetration testers to sit in between a web server and a browser to inspect information like network traffic, assess and exploit vulnerabilities, and find other security issues in applications.
Also read: Getting Started with the Burp Suite: A Pentesting Tutorial
- Wireshark: This open-source tool is designed for network monitoring. Using Wireshark, penetration testers can automatically read real-time data from different types of networks.
- John the Ripper: John the Ripper is a free password-cracking tool that supports several operating systems. JtR is used by penetration testers who gain access to a user’s password hash to decipher the encryption and obtain the password in clear-text quickly.
Penetration testers use several more tools. Some are standard tools for all kinds of testing, while others are used for specific niche cases. Penetration testers must know what the best tool and technique should be used in each scenario. However, this is just one step in the process. Several steps are required even after the assessment is over.
For more on the vast array of available pentesting tools, see the Best Penetration Testing Tools.
What to Do After a Penetration Test
Penetration tests do not end after white hat hackers detect and exploit the vulnerabilities. Reporting and remediation are vital components that should never be left out. Top pentest vendors offer complete reports that provide a 360-degree view of the errors, the consequences, and recommendations to fix and patch security flaws.
Reporting also serves the security teams, IT, developers, workers, and top decision-makers. The entire work of the organization and its performance should be enhanced through reporting. The main goal of penetration tests is not to detect weaknesses but to improve efficiency and security and prevent risks.
In addition, a good practice for penetration testers and organizations is to restore systems to the original state in which they were before an attack. If pentesters modify configurations and settings, install software, or make any other alterations to the system, they must clean and restore it.
Additionally, companies running penetration tests should be executing them within their pentest program and frameworks. After remediation, the pentest teams should monitor the security upgrades and patches and prepare to run the next scheduled test. Penetration testing is not a one-and-done process; it’s continual work that has several benefits when done correctly. However, there are also some challenges.
Read more on how to protect your network from malicious actors and other threats.
Pros and Cons of Penetration Testing
Like all security solutions and approaches, penetration tests have benefits, risks, and challenges. It is essential to know and understand the pros and cons of penetration testing when implementing a program in your organization.
| Pros | Cons |
|---|---|
| Automated security technology cannot mimic hackers’ techniques in real life. Therefore, penetration testers are vital in providing technical insight into what attackers can do. | Hiring security professionals or consultants can be expensive. Organizations should ensure they have the proper budget to hire a penetration tester. |
| Penetration tests are also flexible and can be customized. This allows organizations to test different scenarios and adapt to modern threats as they are released into the wild. | The efficiency of the test will depend on the penetration testers and their skill sets. Therefore, companies should research potential penetration testers to determine whether or not they possess the right level of skills and experience. |
| Most penetration testers offer remediation recommendations for their findings. This allows organizations not to understand not only where their weak points are but also how to fix them and take action. | Scans and exploits performed on a network or application can disrupt normal operations if not carefully managed. |
Bottom Line: Hire the Good Hackers
Penetration testing is a critical cybersecurity practice that can find security holes before hackers do. Along with threat hunting, it’s a practice that can’t be done by tools alone; it requires a human element. And those people need to be trained and prepared to do the job right. It’s not a manageable undertaking, but it’s one that every organization should do to the best extent possible.
Interested in checking out some free tools to see what penetration testers do? Check out our list of the Top Open Source Penetration Testing Tools.
