How to Create an Effective Penetration Testing Strategy

  • Team Omega
  • November 1, 2022

As threat actors continue to work overtime to find and exploit companies’ weak points, IT teams must adapt to discover and solve their vulnerabilities first. Penetration testing, also known as pen testing, is a common tactic any company can implement that safely simulates attacks to discover where weaknesses lie, thus producing reports that detail what loopholes or security gaps can be closed. Since this type of testing can be done in a variety of ways, it’s important to strategize how to incorporate pen tests into your budget, making it worth the money and time involved.

Strategize Your Penetration Testing

Begin with Risk Assessment

Rather than conducting penetration testing to simply check a box on your to-do list or to seek out vulnerabilities across your entire system, start first with a risk assessment. By looking at a system-wide risk assessment initially, you can make your pen testing more efficient by identifying which areas are critical or high-value and warrant more attention than others.

Per ISACA’s State of Cybersecurity 2022 Report, social engineering attacks were the most common type of cyberattack, so with risk assessments, IT teams should consider both internal and external threats. Once you have your findings, you can appropriately establish the scope and objectives for your penetration testing, saving time and resources on prioritizing work that won’t truly help or impact your business.

Create a Categorized Schedule

As threat actors continue to employ a variety of tactics to breach a company’s defenses, it’s important to run a variety of penetration tests, each focusing on a different area of your system. Pen testing can be broken down into three different categories; they are:

  • White Box testing is often the most cost-effective type of penetration testing because locating vulnerabilities is easier, saving you time and money in the process.
  • Gray Box testing focuses on the internal side and the damage resulting from an authenticated internal user’s attack. Armed with minimal information, testers imitate an internal attack to gather more specific insights than white box testing.
  • Lastly, Black Box testing is formatted similar to a real-world attack, meaning testers start as a malicious actor would: from nothing. In this form of pen testing, testers are given no data to work off of–other than an authorized attack scope–so they must breach defenses using only what they find. While black box testing may take the most time, it often produces the most accurate results.

Since each penetration test provides different results on the various vulnerabilities present within an organization, create a testing schedule that’s categorized by the type of test. This way, you’ll have a comprehensive view of your internal and external vulnerabilities at any given time.

Factor in Compliance & Regulatory Standards

The ultimate goal of penetration testing is to identify your weak points and vulnerabilities so you can strategize your remediation efforts and increase your overall cybersecurity posture accordingly. However, depending on your industry, an additional goal could be to ensure you’re still achieving compliance and adhering to the regulatory requirements present for your company. The guidelines or frameworks that apply to you could include:

  • PCI DSS,
  • ISO 27000 Series, or
  • the National Institute of Standards & Technology (NIST) Cybersecurity Framework

Turn Insights Into Feedback

While pen testing enables IT teams to reduce and better manage risks, it also produces valuable reports that provide an overview of the efficacy of current vulnerability management and development means. When testing reveals the presence of long-established vulnerabilities or similar vulnerabilities are present across multiple devices, this indicates that reactive procedures need to be updated or proactive processes need to be implemented. Additionally, when cross-application vulnerabilities are found through pen testing, you have the opportunity and new data you need to update your software development training.

Turn to Experts for Help

At each point in your penetration testing, it’s important to understand that everything from conducting your risk assessment to implementing your findings is an incredibly complex but necessary process that requires expert knowledge to do properly. If you don’t currently have the time or resources to establish this internally, you always have the option to bring on third-party experts like those at Omega to help you gain a competitive edge and adapt to the continually evolving cyber threats targeting businesses like your own. With the right experts on your side, you can eliminate unnecessary testing or spending and focus on your business-critical assets instead.

With Omega, we will manage your full cyber resilience lifecycle, conducting risk assessments and updating your pen testing strategy, to ensure your efforts are uncovering and addressing gaps before malicious actors can take advantage of them. Contact the Omega team to book a demo and learn more about how we can help make the most of your penetration testing results today.


ISACA, State of Cybersecurity Report. 2022.