Optimizing Penetration Testing

Optimizing Penetration Testing

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October 15, 2023

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Penetration testing, often referred to as “Pen test,” is a widely recognized practice in the realm of cybersecurity. Its popularity has even transcended the boundaries of cybersecurity, making it a term familiar to those outside the field.

 

Penetration testing involves an authorized cyberattack on a system, network, or application with the primary aim of identifying security vulnerabilities. During a penetration test, the tester attempts to compromise the security of the specified targets using techniques that a malicious actor might employ.

 

Navigating the Landscape of Cybersecurity

Firewatch Solutions was founded to address two prevailing challenges within the cybersecurity industry:

 

  1. The demand for cybersecurity services outpaces the availability of cybersecurity talent.
  2. Transforming cybersecurity into a competitive advantage for rapidly expanding businesses.

 

Our approach to penetration testing takes both challenges into consideration. Through our interactions with various organizations, we’ve observed that many tend to approach cybersecurity in a disjointed manner. They often prioritize well-known surfaces and systems while overlooking the broader security landscape. Additionally, organizations sometimes view penetration testing as a one-size-fits-all solution for cybersecurity, particularly just before deploying products or systems. However, integrating cybersecurity into an organization’s culture is thought to be of greater importance.

 

Penetration Testing in the Software Development Life Cycle

Penetration testing typically occurs after the completion of the feature set in the software development life cycle, often coinciding with User Acceptance Testing. It is commonly conducted in staging or production environments because security vulnerabilities are most relevant when a product or system is nearing its launch.

 

Nonetheless, relying solely on penetration testing may lead to certain issues. Key security controls that could have been implemented earlier are overlooked, and security concerns are identified at a later stage in the development cycle. Late modifications to a product or system can become cost-prohibitive, particularly when incorporating security specifications in functional requirements. It is more cost effective to consider security during architectural design, periodically reviewing code during active development, or adding security checks to intermediate builds.

 

Automation plays a vital role, especially within agile development cycles and dynamic environments. Automation can be shifted left through training and tool adoption. Results from Static Application Security Testing and Dynamic Application Security Testing can be easily verified by the development team and can be seamlessly integrated to activate periodically or in response to actions such as a merge request to a CI (Continuous Integration) branch or a new deployment. This streamlines the mitigation process for issues that can be automatically identified by scanning tools, freeing up limited security resources. There are numerous open-source and commercial solutions available to facilitate this, reducing the barrier to achieving a fundamental level of security. Shifting left is essential to fully realize the value of a penetration test.

 

Organization Risk Evaluation and Focus Areas

If everything is labeled as “high priority,” nothing truly is. Failing to differentiate protection based on business requirements, threats, and risks is a challenge applicable to penetration tests and the enforcement of security controls. A lack of business context in cybersecurity decisions results in increased costs for implementing cybersecurity without commensurate value. Similarly, conducting penetration testing without sufficient consideration of business context, threats, and risks can result in inaccurate representations in risk assessments, criticality evaluations, and misallocation of resources thus eroding trust and credibility in cybersecurity as a value-adding function.

 

This underscores the importance of maintaining open lines of communication with other parts of the organization that possess the necessary business context. Such communication ensures context is forefront so that value is derived from the penetration test.

 

Supplement Penetration Tests with Vulnerability Assessments

While penetration testing can serve as a valuable starting point for cybersecurity initiatives, it should not be the sole line of defense. In addition to penetration testing, consider the following:

 

  1. Periodic automated vulnerability assessments conducted in-house to address gaps between manual tests.
  2. Ensure that threat modeling is incorporated into the penetration testing process and provide the necessary business context for accurate risk assessments.
  3. Do not underestimate threats within internal-facing systems; carefully evaluate whether they should be included within the scope of work.
  4. A white-box assessment, which offers a more comprehensive perspective than that of a casual attacker, can be advantageous.

 

Parting Thoughts

To maximize the impact of your next penetration test, strategically align it with your organization’s top business priorities. In doing so, you’ll pay only for what is essential and achieve results that can enhance your security posture. The effectiveness of a penetration test hinges on the seamless integration of automated security testing with your development or deployment process, as well as on how well the penetration test report aligns with your business objectives.

 

To assess and enhance your organization’s cybersecurity defenses, receive a Penetration Test from Firewatch Solutions. Strengthen your cybersecurity posture and ensure the safety and protection of your digital assets.