7 Best Practices for Penetration Test Planning

Do you know where vulnerabilities are hiding in your environment? Chances are you don’t, and a hacker might just find them for you. It’s a risk you can’t afford to take, but you can prevent it with penetration testing.

By running a penetration test, you uncover cybersecurity weaknesses, study how they can be exploited, and secure them against an attack. Penetration testing is a key part of a security strategy that contributes to protecting from an attack by focusing on vulnerabilities in your environment.

As with any security method, penetration testing requires careful planning. As you implement penetration testing in your environment, follow our seven best practices for effective results.

What is penetration testing

Penetration testing, also called pen testing or a pentest, refers to a security practice where cybersecurity experts simulate a cyberattack on a system. These experts, also called ethical hackers, are hired to find and exploit vulnerabilities in a computer system where attackers could sneak in—all to improve security. While typically done on computer systems and networks, penetration testing can also be done for web and wireless security, mobile and client applications, phishing, and physical boundaries.

Who performs penetration testing

Penetration testing is most effective when performed by an experienced outside service or contractor. By hiring an external resource with little previous knowledge of your systems, you ensure objectivity in the testing process and in exposing vulnerable areas missed by your developers and security team. The service you choose should conduct testing regularly—at least once a year or more frequently, depending on your company’s risk exposure and the maturity of your security implemented controls.

7 best practices for penetration testing planning

Follow these best practices as you plan for penetration testing to ensure an effective and successful outcome.

1. Define your scope and budget

It might make sense to want to test your entire environment, but the cost might convince you otherwise. Therefore, consider your high priority and low priority areas that need penetration testing. High priority areas are where your greatest vulnerabilities exist. Pen testers commonly identify the highest risk points to be operating systems, application code, and configuration files, particularly in software development projects. Lower priority areas include low-to-no-code applications for internal business operations.

2. Include financial and customer data sources

An organization’s data is its biggest asset, particularly in the retail, financial, government, and healthcare industries. Organizations in these industries typically have vast quantities of transactional, customer, and financial data. If your organization has this type of data, conduct comprehensive, full-scale penetration testing on your data sources, especially to meet industry and security regulations. But don’t stop with just the data sources; also test the software that connects to them and its supporting infrastructure.

3. Consider penetration testing remotely accessible resources

Whether you have remote employees, remote building automation systems (BAS), or resources that have remote access, factor each remote endpoint into your penetration testing plan. Some remote resources, such as remote BAS, have limited security functionality, making them an easier target for hackers to gain access to your network. Penetration testers can identify your exposure to external attacks by finding and assessing your publicly accessible assets.

4. Follow a penetration testing methodology

The results of your penetration test can vary widely based on which methodology you follow. Some of the common testing methodologies and standards include:

• Penetration Testing Execution Standard (PTES)
• Payment Card Industry Data Security Standard (PCI-DSS)
• Open-Source Security Testing Methodology Manual (OSSTMM)
• OWASP Web Security Testing Guide
• National Institute of Standards and Technology (NIST) Special Publication 800-115
• Information System Security Assessment Framework (ISAFF)

Choosing a method is important when conducting your own penetration testing. However, as you search for a penetration testing service, consider the methodologies they follow and how they compare to your objectives.

5. Prepare for the test

Once you decide what you need to test and how you’ll conduct it, prepare for the test, for example:

• Know which tests your hosting or cloud provider allows and seek proper authorizations to conduct them.
• Identify team members who will review the test report and fix issues that were discovered during the test.
• Schedule patching to occur after testing is completed and you’ve reviewed the results, unless you need to fix a critical issue that impacts your customers.

Any changes you make during penetration testing can affect the testing environment and your results, not to mention waste your pentest investment.

6. Create a communication plan

Communication is key, even in pen testing. Establish communication protocols between you, your team, and the penetration testing team to ensure a smooth process. Conduct regular meetings so you can monitor progress, ask questions, and exchange other essential information. Choose a single point of contact on your team to be available for any critical information and questions during the test.

Inform your team of the timeframe in which the pentest will happen. However, don’t tell them specifically when it’s in progress to see if they can detect the threats in action.

7. Choose a qualified pen tester

Your penetration testing service provider should fit these criteria at a minimum:

• Uses automated and manual techniques for maximum effectiveness in uncovering vulnerabilities and advanced threats in your environment.
• Examines internal and external IT assets by using commercial, open source, and custom tools to discover rogue or unknown resources that could lead to an attack.
• Explores how high-risk vulnerabilities can be exploited to determine the impact on your operating environment and feasibility of a potential breach.
• Minimizes false positives through further validation and vetting.
• Generates custom reports that highlight the risks of identified and exploited vulnerabilities and offers corresponding strategic mitigation, recommendations, and actionable insights.

The more vulnerabilities your service provider uncovers, the better off your organization is by knowing what to fix before a hacker exploits them.

Pen test your environment with confidence

For best results of your penetration test, follow the recommended practices highlighted in this post. Most importantly, choose a qualified, reputable penetration testing service. Check with colleagues or investors for recommendations to begin your search and make sure the service you choose aligns with your objectives for testing.