The Pitfalls of Periodic Penetration Testing & What to Do Instead
Erik HolmesErik Holmes

The Pitfalls of Periodic Penetration Testing & What to Do Instead

Periodic penetration testing approaches can be likened to regular tire inspections for vehicles. While they provide valuable insights into the condition of your tires during each check-up, they cannot help you identify any potential issues that may arise in between inspections.

By Erik Holmes, CEO, Cyber Guards

Organizations often rely on traditional approaches like snapshot in time-based penetration testing to mitigate the risk of cyber attacks. However, these methods have limitations and may not comprehensively understand the organization’s security posture.

In this article, we will explore the pitfalls of periodic penetration testing and suggest adopting a continuous testing approach and implementing attack path management to enhance your organizations cyber defense strategy.

The constraints of snapshot in time penetration testing

Periodic penetration testing has been a standard practice for many organizations, but is it the best approach for cybersecurity assessment? One major constraint of this method is that it can only provide a snapshot of the organization’s security posture at a specific point in time. This means new vulnerabilities arising after the testing period will be left undetected. Case in point, according to the 2022 Cost of a Data Breach report, it takes an average of 277 days to identify and contain the breach.

Another limitation of periodic penetration testing is its reliance on time-based testing, where testers are given a specified amount of time to identify vulnerabilities. This approach does not account for some of the more complex and advanced attacks that may require additional time to uncover.

Traditional penetration testing involves manual testing by security experts with varying skill levels. This snapshot testing adds a constraint on the accuracy of the results, which significantly depends on the testers capabilities. A single mistake or oversight from the testers can lead to costly breaches.

Lastly, periodic penetration testing offers limited scope when assessing an organization’s entire security landscape. The manual testing process can only cover specific areas of the organization’s network, leaving other areas untested.

How to embrace continuous cybersecurity testing

While periodic penetration testing can provide a snapshot of your organization’s security posture, it often fails to account for the dynamic nature of cyber threats. Organizations must continuously test their security measures to effectively mitigate risks to identify and neutralize emerging threats in real-time.

Organizations can leverage various approaches and tools to implement continuous cybersecurity testing, such as the Atomic Red Team by Red Canary, an open-source library of tests mapped to the MITRE ATTACK framework that security teams can use to simulate adversarial activity and validate their defenses. These tools can help prioritize and mitigate potential cyber-attacks by automating security testing and providing valuable insights into adversary tactics and techniques.

Endpoint security testing and firewall testing are excellent starting points for implementing continuous cybersecurity testing. By simulating phishing emails, running PowerShell commands at endpoints, and monitoring VPN logins at the firewall level, organizations can proactively identify potential vulnerabilities and mitigate them before cyber attackers can exploit them. Proofpoint’s 2021 State of the Phish Report revealed that 57% of organizations dealt with at least one successful phishing attack in 2020. These statistics underline the importance of continuous cybersecurity testing, particularly in the area of simulated phishing, to detect and mitigate such threats promptly.

Ultimately, embracing continuous cybersecurity testing is vital to securing your organization and safeguarding your valuable assets. With the right tools and strategies, organizations can identify and neutralize threats in real-time, stay ahead of the curve, and protect their systems and data from cyber threats.

The role of attack path management in cyber defense

The role of attack path management in cyber defense cannot be overstated. Attack path management takes a contextual and holistic approach to protecting critical assets in a way that traditional security solutions do not. While continuous security testing evaluates controls in place, attack path management takes a more comprehensive view to identify an organization’s most critical assets and networks.

Attack path management can help organizations understand their business operations deeply, identifying the most vulnerable areas requiring more security measures. By pinpointing areas within a network where sensitive data, such as PHI or PII, may exist, attack path management can help organizations identify and eliminate risky pathways that attackers can use to target valuable assets. This is particularly important in today’s environment, where the interconnectivity of networks makes identifying and mitigating potential attack paths incredibly challenging.

While continuous security testing plays a vital role in cybersecurity by evaluating the effectiveness of security controls, sometimes the testing can miss vulnerabilities or gaps in the network. Attack path management fills this gap by providing context to your security environment, allowing a more complete and accurate assessment of your defense mechanisms.

To embrace attack path management in your organization without causing harm to your system’s environment, Cyber Guards suggests platforms like XM Cyber for Attack Path. It’s important to note that organizations should not test in a production environment without permission.

Attack path management and continuous security testing complement each other effectively. By adopting both methodologies, organizations can assess their vulnerabilities comprehensively, eliminate potential attack paths, and fine-tune their defense mechanisms confidently. Ultimately, this will help organizations improve their cyber defense posture, reduce the risk of successful attacks, and protect their critical assets and data.

Embracing Innovation: Approaches for Comprehensive Cybersecurity

Embracing continuous cybersecurity testing can help organizations stay one step ahead of threat actors by ensuring no gaps in their understanding of their security posture, making it much more difficult for attackers to find and exploit security weaknesses. Furthermore, complementing continuous testing with attack path management allows organizations to take a contextual approach to protect their critical assets, fine-tuning their defense mechanisms and reducing the paths attackers might use to target valuable assets. By exploring innovative approaches beyond traditional methods to safeguard against potential security breaches, organizations can confidently navigate the ever-changing landscape of cybersecurity and mitigate risks more comprehensively.

About the Author

The Pitfalls of Periodic Penetration Testing & What to Do InsteadErik Holmes is the chief executive Officer at Cyber Guards, a Memphis-based managed cybersecurity services company. Erik brings an impressive dossier to the table, from serving in SEAL Team Six to holding key positions at BlackHorse Solutions and Deloitte Consulting. Drawing from this rich experience, Erik offers profound insights into cybersecurity.

Erik can be reached at [email protected] and at Cyber Guard’s website

April 8, 2024

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