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Pen Testing for Compliance Only? It's Time to Change Your Approach. 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. The importance of continuous pen testing Embracing continuous security testing offers organizations numerous benefits. 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.