6 Penetration Testing Best Practices for Enterprises

Penetration Testing Best Practices for Conducting Effective Penetration Tests on Enterprise Networks

February 28, 2023
| David Tidmarsh
| Penetration Testing

Penetration testing is an invaluable addition to any organization’s cybersecurity toolset. By conducting regular penetration testing, enterprises can discover and patch security issues before hackers detect and exploit them.

However, not all penetration testing methods and strategies are created equal. This article will discuss everything you need to know about penetration testing best practices: the benefits and techniques of penetration testing for enterprises, how to perform penetration testing planning, and how to get started in your career as a pen tester.

What is Penetration Testing?

Penetration testing or pen testing simulates cyberattacks and intrusions on a computer system or network to test its defenses and identify vulnerabilities. A person who carries out penetration testing is known as a penetration tester or pen tester.

By discovering potential weaknesses in an IT environment, penetration testers aim to mitigate or resolve these problems before malicious actors can take advantage of them. Penetration testing can assess the security of a wide range of IT systems, including networks, servers, web applications, mobile devices, and cloud computing.

6 Different Penetration Tests for Enterprises

Depending on the enterprise’s scope, focus, and goals, there are multiple types of penetration tests that pen testers can perform. Below are some common types of penetration tests for enterprises:

  1. External testing simulates an attack on an organization’s external IT systems and networks. These include its website, public web applications, and servers and network infrastructure exposed to the Internet.
  2. Internal testing simulates an attack on an organization’s internal IT systems and networks. These include its internal network infrastructure, servers, workstations, endpoints, and internal software applications.
  3. Web application testing focuses on an organization’s web applications and website. Penetration testers look for vulnerabilities such as cross-site scripting (XSS), SQL injection, and remote code execution.
  4. Mobile application testing focuses on an organization’s mobile applications. Penetration testers look for vulnerabilities such as insecure data storage, weak authentication and authorization, and lack of encryption.
  5. Cloud penetration testing focuses on an organization’s cloud computing infrastructure. Penetration testers look for vulnerabilities such as unsecured access points, misconfigured cloud resources, and unpatched software.
  6. Social engineering tests attempt to trick employees into divulging sensitive information or breaching security protocols. These may involve phishing emails, phone calls, text messages, or other impersonation schemes. Pen testers may search through a company’s trash or drop a USB stick containing malware in the parking lot to see if a curious employee plugs it in.

4 Benefits of Penetration Testing for Enterprises

Penetration testing is tremendously useful for evaluating and improving enterprise IT security. The benefits of penetration testing for enterprises include the following:

  1. Defending against cyberattacks: The most obvious benefit of penetration testing is that it significantly decreases the likelihood of a devastating cyberattack or data breach that causes significant financial and reputational damage. Penetration testing identifies and swiftly fixes vulnerabilities and weaknesses in an enterprise’s IT infrastructure, making it harder for intruders to enter.
  2. Prioritizing risks: Penetration testers produce reports on which security vulnerabilities are present in the enterprise, offer guidance on how to fix them, and which are most dangerous. It can provide a clear roadmap for mitigating cyber risk, allowing organizations to triage their security flaws by first addressing the most critical ones.
  3. Showing the big picture: Rather than hunting for specific vulnerabilities, penetration testing aims to scan for and identify all potential security holes in an enterprise IT environment. This “big picture” view shows organizations how malicious actors can string together a sequence of smaller-scale weaknesses in their systems to construct a plausible plan of attack.
  4. Regulatory compliance: Depending on the industry, penetration testing or similar methods may be a requirement of specific laws, regulations, and standards. For example, organizations that comply with the PCI DSS standard for payment card security must perform external and internal penetration testing at least once a year, according to PCI DSS Requirement 11.3.1 1-3 (Baykara, S. 2020).

6 Penetration Testing Best Practices for Enterprises

With so many possible techniques and approaches at pen testers’ fingertips, enterprises must perform penetration testing planning to enjoy the benefits of their work. Below are some penetration testing best practices that organizations should follow:

  1. Scope and budget: Enterprises should clearly define the goals and scope of the penetration test, including specific systems, networks, and assets that will be tested. In some cases, the available budget will limit the testing scope.
  2. Laws and permissions: Penetration testing should only proceed with the full consent and authorization of the target. Be sure to follow all applicable laws and regulations before, during, and after the test.
  3. Effective preparation: The most effective penetration tests involve a mixture of automated and manual techniques to thoroughly evaluate an enterprise IT system’s security. Pen testers may also use social engineering to fool employees into disclosing confidential information. Frameworks such as the OWASP Web Security Testing Guide can help penetration testers decide what to test and how to test it (OWASP, 2023).
  4. Incident response: Once penetration testers have uncovered significant vulnerabilities in an enterprise IT system, the organization should follow proper incident response protocols to address and patch them. This involves containing the issue, eliminating the threat, and recovering from the incident to prevent similar problems in the future.
  5. Post-test reporting: Penetration testers must prepare detailed reports about the results of testing, including any vulnerabilities discovered and their recommendations for handling these flaws. Key decision-makers can then use these documents for both short-term incident response and long-term strategic planning.
  6. Tracking new developments: Cybersecurity and penetration testing are constantly evolving as new attack methods emerge and new strategies and defenses appear to mitigate them. Penetration testers should stay up-to-date with new tools and developments in their field to stay ahead of the attackers.

How to Get Started with Penetration Testing

As cybersecurity becomes an even greater concern for enterprises, pen testers and penetration testing planning will play a crucial role in defending an organization’s IT assets. The U.S. Bureau for Labor Statistics expects the demand for penetration testers and other IT security analysts to grow by 35 percent between 2021 and 2031, significantly faster than the average occupation (U.S. Bureau of Labor Statistics, 2022).

Obtaining a penetration testing certification is an excellent way to demonstrate your expertise and start your career in cybersecurity. EC-Council’s Certified Penetration Testing Professional (C|PENT) certification program provides the theoretical knowledge and practical experience you need to hone your penetration testing skills.

C|PENT students learn the essential penetration testing concepts across a variety of domains, from networks and web applications to the Internet of Things and cloud computing. Get in touch with us today to learn more about the C|PENT certification and jumpstart your path to a penetration testing career.


Baykara, S. (2020, April 7). PCI DSS Requirement 11 Explained. PCI DSS Guide. https://www.pcidssguide.com/pci-dss-requirement-11/

OWASP. (2023, January 6). OWASP Web Security Testing Guide. https://github.com/OWASP/wstg

U.S. Bureau of Labor Statistics. (2022, September 8). Occupational Outlook Handbook. Information Security Analysts. https://www.bls.gov/ooh/computer-and-information-technology/information-security-analysts.htm

About the Author

David Tidmarsh is a programmer and writer. He’s worked as a software developer at MIT, has a B.A. in history from Yale, and is currently a graduate student in computer science at UT Austin.

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