Continuous Penetration Testing: Why One-Time Pentests Are Becoming "Old School"

By
Jack Ekelof
,
VP Sales & Marketing
Contents

In the ever-evolving landscape of cybersecurity, continuous penetration testing emerges as a strategic response to the limitations posed by the traditional, one-time approach. Unlike its old counterpart, which often  was all the security budget allowed. Boxed in security teams to only receive an adversaries perspective once a year. Continuous penetration testing delivery options have greatly expanded from an ethical hacker and a script kiddie to platforms and people that combine to drive significant risk reduction for the enterprise. 

This continuous methodology involves frequent and iterative testing, allowing security teams to catch vulnerabilities as they arise and effectively seal gaps before they are exploited. By harnessing the power of automation and regular human expertise, organizations are equipped to adapt to new threats. 

Moreover, continuous penetration testing aligns perfectly with modern compliance requirements. As regulatory landscapes tighten, businesses are compelled to demonstrate robust security practices. Regular audits can affirm compliance, but the dynamic nature of continuous testing goes a step further, proving a far more compelling case for resilience.

While the shift towards continuous penetration testing offers numerous advantages, it is not without its challenges. Integration with existing workflows and systems can be complex, often requiring the correct partner to have the right integrations to ticketing and security tools. Resource allocation is another consideration, as it demands a broader set of resources both in initial setup and ongoing management. However, the benefits of continuous adaptation and detailed reporting typically outweigh these initial hurdles. As security teams are able to space out the critical vulnerabilities versus the pdf report dump on the current pentesting cadence. 

Ultimately, the choice between traditional and continuous penetration testing hinges on an organization’s security goals and risk tolerance. Yet, with the number of vulnerabilities expanding daily, the traditional one-time approach may soon fade into obsolescence, making way for its more dynamic and adaptive successor.

Understanding Continuous Penetration Testing

In today’s rapidly evolving cyber landscape, continuous penetration testing stands out as a proactive security measure. Unlike traditional methods, which offer a snapshot of your security posture at a single point in time, continuous penetration testing is akin to having a vigilant guardian constantly scouring your environment for weaknesses. This ongoing process integrates both automated tools and human expertise to ensure vulnerabilities are identified and addressed swiftly, enhancing your organization's resilience against cyber threats. 

With the frequency of cyber threats on the rise, the value of real-time insights cannot be overstated. Continuous penetration testing not only aligns with the pace of modern software development cycles but also adapts to the shifting demands of your firewall vendors that are under constant probing. Through regular assessments, it supports the identification of security gaps as soon as they occur, allowing for immediate mitigation and remediation strategies to be implemented. 

Moreover, this approach empowers cybersecurity teams by facilitating the discovery of vulnerabilities early in the deployment of new CVE's that have evidence of public exploitation. It lays the groundwork for building robust cyber programs from the start, thereby reducing the risk of costly breaches. Businesses can no longer afford to rely on sporadic checks; continuous vigilance is essential to maintaining a robust security foundation in a world where threats evolve with alarming speed.

"Old School" Pentest vs. "New" Continuous Penetration Testing 

Type "Old School"
One Time Pentesting
Continuous Penetration Testing
Scheduling  Typically compliance required testing is scheduled weeks out and occurs within a set time frame per scope of pentest.  Continuous Recon & Discovery takes occurs year round, and as new assets and vulnerabilities appear. Human Pentesters are surged & testing in real time. 
Platform + Human Effort  Manual  Automation + Manual Testing
Intelligence Human Led  Platform-Led + Human Intelligence
Reporting 1 Static report is delivered via PDF, or Excel  Platform based reporting that provides real time dashboards, and includes all static reports for compliance objectives
Compliance Meet's Requirement Generates resilient cyber defenses that encompass compliance outcomes for PCI, HIPPA, SOX,SOC2, ISO, DORA, & CMMC.
Communication   Limited to kick off & report read out calls, and escalation of critical findings are delayed  Slack, and Teams channels that facilitate year round communication with an Offensive SOC. 
Remediation  All vulnerabilities delivered at once can overwhelm patching teams, akin to eating an elephant in one go. Remediation Prioritization that expidites Mean Time to Remediation (MTTR)
Commercials Project Based  Subscription Based 

Why Are Organizations moving One Time Pentesting Budgets to Continuous Pentesting Strategies ?

There’s a shift happening in the cybersecurity landscape, and it’s all about stepping up the game from static, one-off assessments to dynamic, ongoing vigilance. Organizations are realizing the numerous advantages of reallocating their one-time pentesting budgets toward a more continuous approach. Let’s dive into these compelling reasons: 

Early Vulnerability Detection:

⦁ Moreover, continuous penetration testing helps in regularly assessing your security controls, ensuring they remain effective against evolving cyber threats. This ongoing vigilance is a game-changer in maintaining a strong security posture.

⦁ Another significant advantage is the constant adaptation to new methodologies hackers might employ. With continuous updates and assessments, your defense mechanisms are better equipped to handle sophisticated attack strategies.

⦁ Continuous testing also minimizes the window of exposure. By identifying vulnerabilities at each development stage, it reduces the risk of security incidents that might disrupt business operations or damage your reputation.

⦁ In conclusion, adopting continuous penetration testing isn't just about staying ahead of threats—it's about fostering a security-first mindset that can transform how your organization handles cyber risks. While one-time testing provides a snapshot, continuous engagement offers a dynamic security landscape, aligning with the rapid pace of technological advancement.

Improved Security Posture:

⦁ Incorporating continuous penetration testing ensures that vulnerabilities are identified promptly, allowing for immediate action before any potential exploit. Unlike one-time testing, which may miss changes made after the test, continuous testing is dynamic and adapts to the evolving security landscape. This adaptability means you're always a step ahead, making your systems less appealing to would-be attackers. 

⦁ Moreover, continuous pentesting integrates seamlessly with modern DevOps cycles, embedding security into the hustle of rapid development processes. This creates a security-first mindset and culture within your organization, where development and security go hand in hand. By being proactive rather than reactive, you build a sustainable security framework that's prepared for the challenges of tomorrow. 

⦁ Combining these efforts with continuous monitoring can further increase your resilience to cyber threats. This holistic approach creates a comprehensive security strategy that's not just about addressing threats when they arise but preventing them from gaining a foothold in the first place. In essence, continuous penetration testing isn't just a tool—it's a philosophy of ongoing improvement and vigilance that empowers your organization.

Reduced Risk of Security Incidents:

⦁  Continuous penetration testing doesn’t just mitigate risks; it actively identifies them before they escalate. By maintaining an ongoing assessment of your systems, you ensure that vulnerabilities are dealt with proactively rather than reactively. This approach provides a dynamic defense mechanism that adapts to emerging threats, helping to fortify your organization’s cyber defenses.

⦁ Think of it as having a vigilant security team that's constantly on the lookout, ready to fend off any unauthorized attempts, rather than just waiting for an incident to occur. As cyberattack strategies continue to evolve, so must our strategies to counteract them. Embracing continuous testing ensures you’re not simply closing the gap on threats but effectively bridging them, thereby minimizing your attack surface and enhancing your resilience against cyber threats.

Compliance Adherence:

⦁  One-time pentesting, in contrast, can leave significant gaps in compliance, potentially exposing your organization to hefty fines and legal repercussions due to its sporadic nature. By shifting to continuous pentesting, your business benefits from real-time feedback, allowing you to swiftly remedy any vulnerabilities before they become bigger issues. Plus, as new regulations are enacted, continuous testing adapts to these changes, ensuring that your compliance status is always aligned with the latest requirements. This proactive approach is crucial not just for maintaining trust with your customers and stakeholders but also for safeguarding your organization’s reputation. In such a dynamic environment, a continuous strategy is not just a better option—it’s becoming the industry standard.

Enhanced Incident Response Capabilities:

⦁ Continuous monitoring supports threat intelligence. By continuously analyzing data specific to your environment, you gain insights that help anticipate potential threats before they can manifest into significant breaches.

⦁ Moreover, integrating continuous penetration testing with your security measures enhances your organization's overall resilience. This process is not static; it evolves with emerging threats, ensuring that your defenses are always robust and up-to-date. 

⦁ Through ongoing analysis and testing, you are not only preventing potential intrusions but also reinforcing the trust your clients and partners place in your organization. Trust, after all, is built not just on results, but on consistent and transparent efforts to safeguard digital assets.

In embracing continuous pentesting, organizations are not just ticking a box for compliance or following a trend—they’re investing in a more robust, adaptive, and responsive security strategy that meets the demands of today’s fast-paced digital world. It’s about smarter resource allocation, more effective threat management, and securing peace of mind in an unpredictable landscape.

Top Tips for Effectively Adopting Continuous Penetration Testing 

Embarking on the journey of continuous penetration testing requires a shift not just in your security strategy but also in how you think about ongoing vulnerability management. Here are a few tips to ensure a successful adoption: 

Set Clear Objectives: Define what you aim to achieve with continuous penetration testing. This could range from reducing Mean Time to Respond (MTTR) to enhancing your proactive threat detection.

Invest in the Right Tools: Opt for tools and platforms that provide seamless integration with your existing systems. These tools should be capable of automating repetitive tasks while still allowing for expert human oversight.

Build a Skilled Team: While automated tools are vital, the expertise of professionals can’t be underestimated. Ensure your team has the necessary skills to interpret data and respond to threats.

Foster Collaboration: Continuous penetration testing is not just an IT concern. Encourage collaboration between development, operations, and security teams to create a cohesive security culture.

Regularly Review and Adapt: Cyber threats evolve, and so should your penetration testing strategies. Regularly update your methods and tools to align with the latest threat landscape.

Communicate Findings Effectively: Ensure that the reports from continuous testing are clear, concise, and actionable, enabling stakeholders at all levels to understand and act upon the insights.

By taking these steps, you can unlock the full potential of continuous penetration testing, leading to a more robust and responsive security posture. Remember, the goal is not just to identify vulnerabilities but to build an ecosystem that supports safe and sustainable growth.

Integration with Attack Surface Management 

In today's rapidly evolving digital landscape, the perimeter of what's considered an organization's attack surface is continually reshaping. Attack Surface Management (ASM) plays a pivotal role in maintaining an updated understanding of this attack surface, focusing primarily on critical assets. By integrating Continuous  Penetration Testing with ASM, organizations can ensure that security efforts are both comprehensive and focused on the most vulnerable points. 

This integration enables an ethical hacker based approach to ASM, where ASM tools are tasked with continuously monitoring and analyzing an organization's digital footprint. It identifies vulnerable assets and prioritizes them for security measures based on their criticality. This prioritized scanning means that your security team can focus on the areas that matter the most, deploying resources more effectively. 

Moreover, pairing continuous pentesting with ASM also involves collaboration with Red Teaming exercises. This enhances resilience against cyber threats by simulating real-world attack scenarios, allowing security teams to test and validate their defenses in a controlled environment. Such exercises complement the detailed insights gained from ASM tools, leading to a stronger, more informed security posture. 

Process of Evolve Security Continuous Penetration Testing 

1. External Pentest 

Conducting a comprehensive penetration test across all assets within scope satisfies the compliance testing needs for PCI/DSS, Cyber Insurance, SOC2, CMMC, HIPAA, and DORA requirements.

2. Attack Surface Baselining 

As the pentest commences, the Darwin Attack Platform initiates asset discovery and maps all external assets. This includes external networks, web-facing applications, and cloud services like Azure, Google, AWS, and O365. Any findings are verified by US-based experts from Evolve Security's Offensive Security Operations Center. This process helps confirm an organization's assets, including shadow IT, unidentified infrastructure, and misconfigurations.

3. Continuous Attack Surface Discovery 

Daily event based automated discovery & valdiation from attacker perspective. Continuous discovery of external assets that are impacted by CVE's. 

4. Continous Manual Pentesting

Engage in proactive manual penetration testing to assess how exploitable identified vulnerabilities are. An expert review of these findings is conducted before communicating with you, ensuring high-impact attack paths are closed for your organization swiftly and effectively.

5. Quarterly Reporting

Quarterly summaries of vulnerability findings reflect changes from the previous reporting period, showcasing due diligence every three months. This summary translates risks for audiences beyond IT and IS departments.

How Evolve Security Can Help 

At Evolve Security , we specialize in human tester-driven continuous penetration testing that ensure your IT security teams gets in front of attack vectors that could impact the organization your team protects. 

From validating vulnerabilities to reduce false positives to finding cloud misconfigurations, our team helps organizations turn attack surface visibility into prioritized security teams. 

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Unlock your organization's full security potential and uncover even more vulnerabilities than before by choosing our advanced penetration testing services.