Imagine this: Your organization completed its annual penetration test in January, earning high marks for security compliance. In February, your development team deployed a routine software update. By April, attackers had already exploited a vulnerability introduced in that February update, gaining access to customer data weeks before being finally detected.
This situation isn’t theoretical: it plays out repeatedly as organizations realize that point-in-time compliance testing can’t protect against vulnerabilities introduced after the assessment. According to Verizons 2025 Data Breach Investigation Report, the exploitation of vulnerabilities rose 34% year-over-year. While compliance frameworks provide important security guidelines, companies need continuous security validation to identify and remediate new vulnerabilities before attackers can exploit them.
Here’s what you need to know about pen testing to meet compliance standards — and why you should adopt continuous penetration testing, if your penetration testing goals go beyond minimum standards.
The current state of pen testing
Compliance-driven pen testing
If your organization is like many, you might conduct penetration tests primarily to satisfy regulatory frameworks like PCI DSS, HIPAA, SOC 2, or ISO 27001. But if your pen testing focuses on simply checking off compliance boxes — instead of developing comprehensive security postures — you’re creating a dangerous disconnect between security theater and actual threat protection.
Limitations
Compliance-focused pen testing has several limitations that leave organizations vulnerable.
- Surface-level security: Compliance-focused penetration testing typically addresses only compliance-relevant vulnerabilities. If your organization focuses its pen testing exclusively on meeting compliance requirements, you’re just scratching the surface — and missing the chance to identify vulnerabilities that fall outside the scope of regulatory frameworks. These undetected weaknesses can give attackers an attack vector into your systems, potentially leading to devastating data breaches and operational disruptions.
- Static nature: Cyber attackers and the digital landscape move fast. Compliance standards? Not so much. During the months (or years) it takes for regulatory frameworks to catch up with new threats – and the gaps between compliance-focused penetration tests – malicious actors are actively developing exploits for emerging vulnerabilities. By the time these weaknesses appear on compliance checklists, attackers may have already compromised countless systems.
- False sense of security: Organizations often mistake compliance for security, believing a passing audit score means they’re sufficiently protected. But the reality is that compliance certifications represent minimum standards that sophisticated attackers can easily bypass. Companies with successful audits may lower their guard when they should be working on strengthening their defenses beyond basic requirements.
The importance of continuous pen testing
Embracing continuous security testing offers organizations numerous benefits.
- Beyond compliance: Proactive and continuous penetration testing can reveal vulnerabilities that scheduled compliance checks might miss. Skilled human testers can uncover complex security flaws in business logic, authentication systems, and data flows, while automated scans keep an eye on any changes that might happen over the development cycle. By implementing regular, comprehensive testing, your organization can stay ahead of attackers rather than merely satisfying auditors. You’ll be doing much more than passing the next compliance review — you’ll be developing a resilient security posture capable of withstanding more sophisticated threats.
- Continuous improvement: Security threats constantly change, forcing organizations to adopt ongoing testing instead of point-in-time assessments. And regular penetration tests can expose vulnerabilities before attackers can exploit them. For example, Pen Testing as a Service (PTaaS) helps organizations achieve continuous security validation without overwhelming internal teams. With PTaaS, your organization can detect new threats in time and quickly take steps to remediate them. Instead of reacting to breaches after they occur, PTaaS lets you stay a step ahead of attackers by using real-world testing to continuously strengthen your security.
Key components of a pen testing strategy with security in mind
To implement penetration testing that truly helps safeguard your systems, focus on these key strategic components:
Regular or continuous testing
To effectively address vulnerabilities in real time, your organization should regularly conduct penetration tests — including after significant system changes and before major deployments. Ultimately, your ideal pen testing frequency and depth will depend on your assets — their complexity, criticality to your business operations and external exposure.
For example, if you have an online store that holds critical customer data and payment information — and is regularly updated with changes and plugins — you may want to employ continuous testing. On the other end of the spectrum, your marketing department’s fall-campaign microsite may only need quarterly or annual assessments.
Integration with other security measures
Want to maximize your organization’s security effectiveness? Combine penetration testing with External Attack Surface Management (EASM). By identifying your digital footprint and testing critical applications based on the latest threat data, your team can prioritize high-risk vulnerabilities while ensuring no internet-facing assets remain unmonitored, unprotected or untested.
Customization and threat-led penetration tests
Your organization faces unique security challenges based on your industry, technology stack, and business operations. By tailoring penetration testing, you can focus on your business’s specific threat profile — testing the areas where breaches are most likely to occur based on the most active threat actors and those that would cause the most damage — rather than wasting time and resources on cookie-cutter assessments.
Overcoming challenges
Despite the clear benefits, many organizations struggle with common penetration testing implementation challenges related to resources and culture.
Resource allocation
Resource issues — including budget constraints and shortage of qualified security personnel — prevent many organizations from implementing adequate penetration testing programs. But PTaaS and combined discovery and testing services like Outpost24s CyberFlex service solve these challenges by providing access to certified testers through a predictable subscription model, eliminating budget spikes and the expense of maintaining specialized in-house expertise.
Cultural shift
To move beyond compliance-driven security, your organization’s leadership must champion a cultural shift prioritizing continuous testing and proactive risk management. When security becomes embedded in your organizational culture, pen testing transforms from a periodic checklist item into an ongoing process of discovering and addressing vulnerabilities before attackers can exploit them.
Taking action with integrated solutions
For the greatest level of security, your organization must know every application in your environment and test each one thoroughly. And a combined solution like Outpost24’s CyberFlex can help. Integrating EASM and PTaaS on a platform level, allows cybersecurity experts to identify all internet-facing applications, use detailed categorizations to prioritize risks, and test business-critical applications with flexible, human-led assessments. By shifting to proactive penetration testing, your organization can prevent attacks before they happen — and satisfy compliance requirements.
Ready to go beyond compliance and elevate your application security? Request your CyberFlex live demo today.
