What if attackers breach your environment between your pentests? That’s the uncomfortable truth many organizations face today.
The reality is even starker when you look at the data. Our research shows 84% of organizations suffered a cyberattack in 2024, yet only 26% conduct pentests more than once annually. Nearly 20% of CISOs admit they pentest only to meet compliance mandates rather than to improve security. And for those who do test, over 40% say their results are invalid by the time reports are delivered because environments change so quickly.
That means the majority of organizations are leaving months, if not longer, of untested exposure. Annual penetration testing, or even quarterly penetration testing, once considered the gold standard, simply doesn’t reflect the speed of modern threats.
This blog breaks down why annual pentesting is outdated, what the best pentesting cadence looks like, and how organizations can align their security testing frequency with today’s threat landscape.
84%
26%
20%
40%The Legacy of Pentesting
Penetration testing as a discipline has been around since the 1960s, when “tiger teams” probed defense and government systems. But its widespread adoption in business came later, driven largely by compliance pentesting requirements.
Frameworks like PCI DSS, SOC 2, and HIPAA established annual and/or quarterly penetration testing requirements more than a decade ago. For many organizations, this was their first structured exposure to pentesting. At the time, those schedules were reasonable:
- Software was built on slower waterfall development cycles.
- IT infrastructure changed infrequently, with updates rolled out quarterly or even annually.
- Discovered vulnerabilities in commercial software were fewer.
- Attackers had less tools, skills, and motivations.
Annual testing matched the pace of both defenders and attackers. It satisfied regulatory requirements and, for a time, provided real security assurance. But today’s environments, and today’s attackers, move far too fast for that cadence to hold up.
Why Annual (or Quarterly) Testing Is No Longer Enough
Speed of Modern Threats
Our analysis of 50,000 NodeZero® pentests in 2024 found attackers can achieve a critical impact, like domain admin compromise, in as little as 60 seconds. Waiting months between tests leaves massive blind spots.
Point-in-Time Blind Spots
Over 40% of organizations say pentest results are already invalid by the time they receive them, highlighting the futility of point-in-time tests in dynamic environments.
Cloud & DevOps Realities
Over 40% of organizations don’t regularly test their cloud environments, and 31% skip security-focused cloud pentests altogether. In environments where infrastructure changes daily, annual testing falls behind almost immediately. The right pentest cadence for DevOps teams needs to match agile release cycles and hybrid cloud complexity.
Weaponization of Exploits
NodeZero exploited 229 known vulnerabilities nearly 100,000 times in 2024, including dozens on the CISA KEV list — proof that attackers weaponize and exploit weaknesses well before most organizations test again.
So, is even quarterly pentesting enough? The answer is no because attackers move faster than any compliance-driven schedule.
The Case for Continuous Pentesting
Continuous pentesting flips the model from static to dynamic. Instead of waiting months, organizations can validate their security posture as often as needed, even daily.
This shift is powered by autonomous pentesting tools that replicate attacker behavior in real environments, without the time, cost, and constraints of manual-only tests. Modern platforms like NodeZero® Offensive Security Platform integrate seamlessly with agile and DevOps workflows, aligning security testing with how software is actually built and deployed today.
Think of it as moving from annual fire drills to real-time security weakness discovery. Instead of hoping your next compliance test identifies newly emerged weaknesses, you know immediately when attackers could exploit your environment.
Business Benefits of Testing More Frequently
- Reduced Mean Time to Remediate (MTTR): 61% of organizations recognize MTTR as critical, but many struggle to improve it. Frequent testing helps teams validate fixes quickly and reduce exposure windows.
- Lower Cost to Fix: Vulnerabilities caught earlier in the lifecycle are significantly cheaper to remediate.
- Improved Security Posture: By validating fixes immediately, organizations close exploitable gaps and prevent recurrence.
- Risk-Based Vulnerability Management: By focusing on exploitable issues instead of scanner noise, teams avoid remediation paralysis.
- Audit Readiness: Continuous testing creates a living record of due diligence, easing the burden of compliance.
Security teams that embrace a modern pentest frequency aren’t just safer, they’re more efficient and better aligned with business goals.
How Often Should You Pentest?
There is no one-size-fits-all answer. The right cadence depends on:
- Asset Risk Level: Critical systems (finance, healthcare, customer data) demand more frequent validation.
- Regulatory Environment: Compliance frameworks provide a baseline but should never be the ceiling.
- Development Cycle: Agile and DevOps-driven organizations should align web app pentests with deployment velocity.
- Exposure Surface: Internet-facing assets and cloud infrastructure pentesting frequency should match how fast environments change.
At a minimum, organizations should combine monthly automated pentests with annual manual red team assessments for high-assurance coverage.
Real-World Example
Consider an organization that shifted from annual pentests to monthly automated assessments supplemented by targeted, on-demand tests. Within six months, they:
- Reduced exploitable vulnerabilities by over 50%.
- Cut their remediation cycle from months to weeks.
- Saved significant costs by fixing issues earlier in development.
By aligning their pentest frequency with attacker speed, they turned pentesting from a compliance checkbox into a proactive defense strategy. Now imagine the impact if organizations had access to continuous testing—where every new weakness was identified and remediated in near real time.
As one security leader put it:
Modern orgs should treat pentesting like backups: frequent, continuous, and verifiable.”
Conclusion
Annual pentesting belongs to a bygone era. Modern threats demand testing that matches the speed and persistence of attackers. By adopting frequent, scheduled, and on-demand pentesting, organizations gain visibility, resilience, and confidence that annual testing alone can’t provide.
Actionable Takeaways
- Run a baseline pentest now to understand your current exposure.
- Map out your most critical assets and determine a pentest cadence that reflects their risk.
- Integrate continuous pentesting into your DevSecOps pipeline to catch issues before production.
- Educate executives on the risks of delayed testing and the business case for real-time validation.
The question is no longer “How often should you pentest?” The answer is clear: far more often than annually — and ideally, continuously.
Ready to move beyond annual testing?
Schedule a demo to see how continuous pentesting can transform your security posture.