Planning Your Annual Pentest: A Checklist of Penetration Testing Best Practices

Penetration testing, often referred to as ethical hacking, is a vital component in ensuring the security and resilience of any organization’s network, system, or application. A well-executed penetration test offers a firsthand insight into the vulnerabilities in your IT infrastructure, simulating real-world attacks to determine the strength of your defenses. One of today’s penetration testing best practices is to conduct a pentest annually.

But how do you ensure your annual penetration test provides real value and genuinely fortifies your company’s defenses?  Planning for an annual penetration test can be daunting, but following penetration testing best practices can help streamline the process and ensure you get the most out of your testing endeavors. Here’s a checklist of best practices to help you get the best ROI from your next penetration test.

Penetration Testing Best Practices Checklist

1. Understand Your Goals.

“Organizations with more proactive and risk-based vulnerability management, such as vulnerability testing, penetration testing or red teaming, experienced lower than average data breach costs,” reported IBM in their Cost of a Data Breach Report 2023.

Before diving into the logistics of the test, it’s crucial to outline your objectives. What do you hope to achieve? Ask yourself the following questions:

• Compliance Requirements: Is the penetration test a regulatory requirement? If so, what are the specific standards to which you must adhere (e.g., PCI DSS, HIPAA, GDPR)?
• Risk Management: Are you trying to identify vulnerabilities across the entire organization or focusing on a specific department or application?
• Strategic Goals: Are you looking to improve your overall cybersecurity posture, or are you more concerned with safeguarding against a specific type of attack?

Clearly articulated goals will guide the scope and depth of your penetration test and allow you to communicate more effectively with the penetration testing team.

2. Know the Scope of What Needs to be Tested

Your IT infrastructure constantly evolves—and your penetration testing scope needs to evolve with it. One of the most common mistakes organizations make is to pentest the same infrastructure year after year—even after your data moves to the cloud or supplier environments. Defining your testing scope is an often overlooked penetration testing best practice, yet it’s one of the most important steps to achieve your desired results and maximize your cybersecurity ROI. According to IBM’s Cost of a Data Breach Report 2023, 82% of breaches involve data stored in the cloud—and an additional 39% of breaches span multiple cloud environments.

Start by identifying your sensitive data and critical infrastructure, and make sure you include high-value assets in the scope of your penetration test. Consider including the following assets:

• Cloud: If you have high-value data in the cloud, consider including this in your penetration test.
• Networks: Do you need to test your internal network, external network, or both?
• Applications: Which applications are in the scope? Is it your main website, your mobile application, or an internal tool?
• Systems: Are you focusing on specific servers or databases?
• Physical Security: Do you need to test physical access to facilities or data centers?

Mapping out the scope will also allow you to budget adequately for the test. A too-broad scope may inflate costs unnecessarily, while a too-narrow one may not provide enough insight into your cybersecurity posture.

3. Test at an Appropriate Frequency

Even though annual penetration tests are considered a norm, this frequency should be tailored to your environment. In the fast-paced world of technology, a lot can change in a year, making the organization more vulnerable to new types of attacks. A key penetration testing best practices is to determine the appropriate testing frequency based on:

• Rate of Change: Implementation of new features or significant updates to existing ones should trigger a penetration test.
• Industry Standards: Regulations in some industries may require more frequent testing.
• Previous Test Findings: If past tests revealed critical vulnerabilities, it might be prudent to test more often.

4. Choose a Quality Test

Not all penetration tests are created equal. While some tests might only run automated scans, others can include in-depth manual testing by cybersecurity experts. Penetration testing best practices dictate that the quality of the test should align with your goals. Make sure to take into account the complexity of your infrastructure and the sensitivity of the data you’re protecting. A high-quality test often involves:

• Manual Testing: To simulate real-world attack scenarios and discover vulnerabilities that automated tools might miss.
• Automated Scanning: To identify known vulnerabilities quickly.
• Social Engineering Tests: To evaluate the human element of your cybersecurity posture.

There are also different test types to choose from, including:

• Black Box Testing: Testers have no prior knowledge of the system. This simulates an external attack.
• White Box Testing: Testers are given full knowledge and access, simulating an insider threat.
• Grey Box Testing: A blend of both black and white, where testers have limited knowledge.
• Red Team Assessment: A full-scope, multi-layered attack simulation to test an organization’s detection and response capabilities.

Each test offers a unique perspective and will uncover different vulnerabilities and weaknesses. Following penetration testing best practices, a quality test should include both automated scanning and manual testing methods to ensure a wide range of vulnerabilities are identified.

5. Vet the Company Conducting Your Test

Just as you wouldn’t trust an unqualified doctor to diagnose a medical condition, you should be cautious when selecting a penetration testing company. Penetration testing best practices for vetting potential testing companies include:

• Credentials and Certifications: Check if the company and its testers have recognized certifications like GIAC certifications (GPEN/GWAPT), Certified Ethical Hacker (CEH), Offensive Security Certified Professional (OSCP), or Certified Penetration Tester (CPT).
• Reputation and References: Look at reviews, ask for case studies, and request references. Speaking to past clients can give you insights into the company’s professionalism, thoroughness, and communication.
• Methodology: Ensure that their testing methodology aligns with industry standards and penetration testing best practices.
• Communication: The company should provide clear communication before, during, and after the test. A comprehensive report post-test is essential to understand and address your vulnerabilities.

Planning for an annual penetration test requires a strategic approach. By understanding your goals, defining a clear scope, testing at the right frequency, choosing a quality test type, and carefully vetting the testing company, you’re setting your organization up for a successful and informative penetration test. Always keep in mind the penetration testing best practices to ensure that your organization remains secure and resilient against potential cyber threats. If you would like information, please read our cheat sheet of security testing best practices that covers the different types of security tests and the recommended frequency.

We hope you found this information on planning your annual penetration testing best practices helpful! Please contact us if you need help with pentesting. Our expert team is ready to help!