If your team is still doing one annual penetration test and calling it a day, you’re already behind.
Attackers don’t wait for your calendar. New vulnerabilities crop up constantly, and most security teams are stuck chasing the same issues over and over again. The result? Static testing strategies that miss active threats and growing pressure from regulators to evolve. More compliance frameworks are starting to mandate continuous penetration testing to reflect today’s always-on threat landscape.
Always-on security is exactly what continuous penetration testing helps enable, giving teams a way to validate defenses on an ongoing basis and fix what’s broken before someone else finds it.
What Is Continuous Penetration Testing?
Continuous penetration testing is an ongoing process of evaluating an organization’s systems, applications, and infrastructure for vulnerabilities using the same techniques real-world attackers would. Unlike traditional penetration testing, which occurs annually or on an ad hoc basis, good and thorough continuous penetration testing happens regularly, giving organizations a real-time view of their risk landscape.
In today’s threat environment, timing matters. As Anton Abaya, Sr. Director of GRC at Pellera, put it: “There’s so much that can happen in between point A and point B.”
That said, most organizations admit they aren’t confident in their current approach. According to Astra, only 8% of organizations said they were “very confident” in their ability to discover exploitable vulnerabilities with their current testing approach, a strong signal that the status quo isn’t cutting it.
This uncertainty is one reason more organizations are moving to Penetration Testing as a Service (PTaaS), which combines automated scheduling with human-led testing and ongoing reporting. This model allows teams to test new deployments, assess critical systems after changes, and monitor known risk areas on a continuous basis.
Why Is It Important to Continuously Conduct Penetration Testing?
Point-in-time assessments give you a snapshot. Continuous penetration testing gives you a story.
Most organizations are in a constant state of change. Whether it’s a new cloud migration, API rollout, or software update, each shift introduces new risks. Without continuous penetration testing, those vulnerabilities can linger undetected. And the consequences are real – Verizon recently found that 68% of breaches involved vulnerabilities that had been known but left unpatched. That kind of delay simply isn’t sustainable anymore.
Shaun Bertrand, VP of Cybersecurity at Pellera, underscored the stakes: “Companies have been very reactive in this space for years.” To break the cycle, he said, “It’s about using those outputs to mature the program, to move the needle.”
Josh Berry, who leads Pellera’s Red Team, sees the cost of inaction firsthand. “You run the same test six months apart and you get the same results, or worse,” he said. “You’re basically just documenting your negligence at that point.”
4 Key Advantages of Continuous Penetration Testing
1. Better risk reduction and a stronger security posture
Continuous penetration testing helps you catch vulnerabilities as they emerge, not after an attacker has already exploited them. With a real-time feedback loop in place, teams can minimize exposure and harden their environments continuously.
Take the CrushFTP vulnerability (CVE-2023-43177), for example. An unauthenticated remote code execution flaw that caught many off guard. Continuous testing helps detect and close these types of gaps before adversaries can exploit them.
Berry added that many attack vectors haven’t changed much over the years: “A lot of our initial access still comes down to the same weak points, like guessable passwords and Microsoft misconfigurations. It’s new tech, but the same problems.”
2. Faster remediation and stronger response
When testing is built into the SDLC, teams can resolve issues earlier in the development lifecycle. That reduces complexity and boosts accountability.
As attackers shift tactics, organizations often find themselves scrambling to defend the next weak point. “It’s like whack-a-mole,” said Berry. “Clients get good at hardening one thing, like Active Directory Certificate Services, and then we start exploiting another, like SCCM.”
3. Smarter compliance and audit readiness
Continuous testing not only reduces risk, but also generates a steady trail of documented evidence. This makes it easier to prove due diligence during audits and align with frameworks like PCI DSS, HIPAA, and emerging federal cybersecurity mandates.
Regulatory pressure is also building. “We’re seeing pressure from compliance to go from an annual to a quarterly test,” Bertrand said. “If you look at things like the SEC ruling, there’s teeth behind that.”
4. Cost efficiency through prevention
Breaches are expensive. So are incident response efforts. According to IBM, the global average cost of a data breach is now $4.45 million, up 15% over the last three years. By catching high-impact issues earlier and validating fixes quickly, continuous penetration testing helps security teams avoid costly surprises and spread security spend more strategically across the year.
Best Practices for Implementing Continuous Penetration Testing with PTaaS
Adopting continuous penetration testing (CPT) starts with choosing the right PTaaS partner and designing a sustainable process. “We see a lot of clients with good intentions but no real plan,” said Sean Colicchio, Global CISO at Pellera. “Not only do you need clear initial goals for a product or application, but available time for immediate follow-up to validate security fixes. You need a program led by continuous testing to integrate early awareness of improvements into your workflows, which helps get buy-in across teams. Otherwise, even the best tech will fall short early in the process.”
Let’s review how to go about finding the right partner to suit your particular needs.
Define clear goals and scope.
Start by identifying what you want to test and why. Focus on high-risk applications, sensitive data, or customer-facing systems. Align with compliance requirements like GDPR or HIPAA and determine whether you need to test code, infrastructure, cloud configurations, or all of the above.
Choose a provider that blends automation with human expertise.
Look for PTaaS solutions that offer both automated scheduling and expert-driven testing. Automation gives you convenience. Skilled testers provide the nuance, especially when it comes to logic flaws, business logic abuse, or emerging zero-day threats.
Build CPT into your software development lifecycle.
Integrate PTaaS into your CI/CD pipelines to schedule tests automatically during key stages: code commits, pre-production pushes, or new environment spins. The goal is to make security part of how you build, not a box you check after the fact.
Create a dynamic, automated schedule for testing.
“Continuous” doesn’t mean nonstop. It means consistent and responsive. Test more often around major releases, or after incidents. Use your PTaaS to retest quickly after fixes, so you can close the loop and confirm remediation.
Make security collaboration-friendly.
Your developers, security analysts, and ops teams all need visibility. Choose platforms with accessible dashboards and reporting. Encourage direct communication between testers and your internal teams to clarify findings, reduce friction, and resolve issues quickly.
Adapt as your environment evolves.
Your testing strategy shouldn’t be static. Feed threat intelligence and lessons learned from incidents back into your CPT program. Use testing data to spot recurring vulnerabilities or systemic weaknesses. And don’t be afraid to expand or shift your testing scope as your infrastructure and priorities change!
Consider adopting a Continuous Threat Exposure Management (CTEM) approach.
CTEM is a five-stage approach designed to identify, validate, prioritize, and mitigate exposures on an ongoing basis before attackers can exploit them. Penetration testing is recommended within the second stage of CTEM, called discovery, to uncover vulnerabilities and misconfigurations.
Related Read – Why CTEM Is the Future of Security and Easier Than You Think
Always-On Security with Continuous Penetration Testing
Cybersecurity isn’t static. Your defenses shouldn’t be either. Continuous penetration testing has become the backbone of resilient security programs, not just because regulators demand it, but because it actually works.
With the right strategy, partner, and tools, continuous penetration testing can help you move from reactive to resilient, closing the loop between detection, validation, and remediation. You’ll spot issues sooner, fix them faster, and stay one step ahead of what’s next.
Want to see how PTaaS fits into your security program? Contact Pellera to explore continuous testing solutions tailored to your environment.
