Imagine this: your organization will complete its annual penetration test in January and earn a high mark for security compliance. In February, the development team deployed daily software updates. By April, the attackers had already exploited the vulnerability introduced in that February update, gaining access to customer data a few weeks before it was finally detected.
This situation is not theoretical. Deploy repeatedly because organizations understand that point-in-time compliance testing cannot protect against vulnerabilities introduced after evaluation. According to the Verizons 2025 Data Breach Investigation Report, vulnerability exploitation rose 34% year-on-year. Compliance frameworks provide critical security guidelines, but businesses require ongoing security verification to identify and fix new vulnerabilities before attackers can exploit them.
Here’s what you need to know about pen tests to meet compliance standards: Also, why continuous penetration tests should be adopted if the targets for penetration tests exceed the minimum standard.
Current state of the pen test
Compliance-driven pen test
In many cases, organizations may perform penetration testing primarily to meet regulatory frameworks such as PCI DSS, HIPAA, SOC 2, or ISO 27001. However, this is when the pentest focuses not only on turning off the compliance box, but also on creating dangerous pieces between the security theatre and the actual threat protection.
limit
Compliance-focused pentests have several limitations that make your organization vulnerable.
- Surface-level security: Compliance-focused penetration testing typically only addresses compliance-related vulnerabilities. If your organization focuses on pen testing only on meeting compliance requirements, you are only hurting the surface and missing out on the opportunity to identify vulnerabilities outside the scope of the regulatory framework. These undetected weaknesses can impose attack vectors on the system to attackers, which can lead to potentially catastrophic data breaches and operational disruptions.
- Static nature: Cyberattackers and digital landscapes move fast. Compliance standards? Not that much. In a few months (or years), it takes regulatory frameworks to catch up with new threats – and the gap between compliance-focused penetration tests is where malicious actors are actively developing exploits for new vulnerabilities. By the time these weaknesses appear on the compliance checklist, attackers may have already compromised countless systems.
- False sense of security: Organizations often mistake compliance for security. This means that the pass audit score is well protected. However, in reality, compliance certifications represent the minimum standard that sophisticated attackers can easily bypass. Companies that successfully audit can reduce security guards if they should work to strengthen their defenses beyond basic requirements.
The importance of continuous pentesting
Adopting continuous security testing offers many benefits for your organization.
- Beyond compliance: Aggressive and continuous penetration testing may reveal vulnerabilities that may result in scheduled compliance checks being overlooked. While skilled human testers can uncover complex security flaws in business logic, authentication systems, and data flows, automated scanning is turning to changes that can occur in the development cycle. By implementing regular and comprehensive testing, organizations can go ahead of the attacker rather than simply a satisfying auditor. You can do more than pass the following compliance reviews: It will develop a resilient security attitude that can withstand more sophisticated threats.
- Continuous improvement: Security threats constantly change, forcing organizations to adopt continuous testing instead of point-in-time assessments. And regular penetration testing can reveal vulnerabilities before attackers can exploit them. For example, Pen Test as a Service (PTAAS) helps organizations achieve continuous security verification without overwhelming internal teams. PTAAS allows organizations to detect new threats in time and take steps to fix them. Instead of responding after a violation occurs, PTAAS allows attackers to stay one step ahead by using real-world testing to continuously enhance security.
A key component of a security-in-the-box pentest strategy
To implement penetration tests that really help protect your system, we will focus on these key strategic components.
Regular or continuous testing
Organizations should regularly perform penetration tests to effectively deal with vulnerabilities in real time. Ultimately, the frequency and depth of an ideal pentest depends on the asset, its complexity, its importance to business operations, and external exposure.
For example, if you have an online store that holds important customer data and payment information and is regularly updated with changes and plugins, we recommend using continuous testing. At the other end of the spectrum, the Marketing Fall Campaign Microsite may only require a quarterly or annual rating.
Integration with other security measures
Want to maximize your organization’s security? Combines penetration testing with external attack surface management (EASM). Identifying your digital footprint and testing critical applications based on the latest threat data allows teams to ensure that assets aimed at the Internet are not monitored, unprotected or untested, while prioritizing high-risk vulnerabilities.
Customized and threat-driven penetration tests
Organizations face unique security challenges based on their industry, technology stack, and business operations. By adjusting your penetration tests, you can focus on a specific threat profile for your business. This is to test the most active threat actors and the most likely area of damage, rather than wasting time and resources on cookie cutter evaluations.
Overcoming challenges
Despite their distinct benefits, many organizations struggle with the challenges of implementing common penetration tests related to resources and culture.
Resource Allocation
Resource issues, including budget constraints and lack of qualified security personnel, prevent many organizations from implementing appropriate penetration testing programs. However, discovery and testing services such as the PTAAS and Outpost24S CyberFlex service solve these challenges by providing access to certified testers via a predictable subscription model, eliminating the cost of maintaining budget surges and the specialised in-house expertise.
Cultural Change
Beyond compliance-driven security, organizational leadership needs to advocate for cultural change, which is prioritized over continuous testing and proactive risk management. Once security is embedded in the organizational culture, pentests change from regular checklist items to an ongoing process of discovering and dealing with vulnerabilities before attackers exploit them.
Take action with integrated solutions
For the maximum level of security, organizations need to know all the applications in their environment and test each one thoroughly. Also, a combination solution like CyberFlex in Outpost24 is useful. Integrating EASM and PTAA at the platform level allows cybersecurity experts to identify all internet-facing applications, prioritize risk using detailed classifications, and test business-critical applications with flexible, human-driven assessments. By shifting to aggressive penetration testing, organizations can prevent attacks and meet compliance requirements before they occur.
Ready to go beyond compliance and increase security for your application? Request a CyberFlex live demo now.
