If you’re in charge of keeping your organization secure (or just making sure you pass the next audit), you’ve probably asked yourself: How often should we do penetration testing?
It’s a fair question—and the answer isn’t always straightforward. Penetration testing compliance isn’t about checking a box once a year. It’s about understanding what your business needs to stay secure and compliant as you grow and change.
Let’s break it down.
Why Penetration Testing Is More Than a One-Time Thing
Think of penetration testing like a routine health check for your infrastructure. You wouldn’t go years without seeing a doctor—especially if your job, lifestyle, or environment keeps changing. The same goes for your security posture.
Regulators and security compliance frameworks agree. Most require regular assessment as part of ongoing security effort. Why? Because new threats, code changes, and infrastructure updates can introduce fresh vulnerabilities at any time.
What Do the Standards Actually Say?
Many compliance frameworks don’t specifically require penetration testing. However, they do call for regular vulnerability management and security assessments. Penetration testing often fulfills these needs.
Here’s a high-level overview of what key frameworks expect:
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SOC 2: Requires organizations to demonstrate that controls are working effectively, which includes regular testing—typically annually or after significant changes.
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ISO 27001: Recommends annual testing or more frequently depending on risk assessments and changes in the organization’s infrastructure.
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HIPAA: Requires technical evaluations of security controls. While it doesn’t define frequency, annual penetration testing is widely accepted as a best practice.
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PCI-DSS: Mandates external and internal penetration tests annually, and after any significant change to the cardholder data environment.
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FedRAMP: Requires annual penetration testing performed by a third-party assessment organization (3PAO), along with ongoing security monitoring.
How Often Should You Conduct Penetration Testing?
Beyond regulatory and compliance requirements, your ideal penetration testing frequency should reflect your organization’s size, industry, and risk profile. Here are additional key factors to consider:
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Industry regulations: Highly regulated sectors like finance, healthcare, and government often require more frequent testing.
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System complexity: Larger environments with multiple applications, networks, endpoints, and integrations present more potential attack surfaces.
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Change frequency: The more often your infrastructure or applications go through major changes, the more often you should test.
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Risk tolerance: Organizations with high exposure (e.g., providing critical infrastructure or processing of sensitive data) benefit from more frequent assessments.
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Budget constraints: Testing doesn’t need to break the bank—but skipping the necessary tests can be way more expensive in the long run.
To combine both compliance requirements and organizational profiles:
| Framework | Recommended Frequency |
| SOC 2 | Annually at minimum and after major changes |
| ISO 27001 | Annually at minimum |
| HIPAA | Annually or semi-annually, depending on environment and associated risks |
| PCI-DSS | Annually at minimum and after major changes |
| FedRAMP | Annually at minimum and after major changes, plus continuous monitoring |
However, every organization is unique. Working with the right penetration testing companies can help you nail down the right frequency based on your specific needs.
Continuous Security vs. Periodic Penetration Testing
Now let’s talk about something important: performing penetration tests periodically isn’t enough anymore.
Yes, periodic penetration tests are essential—but they only give you a snapshot in time. What about the rest of the year? That’s where continuous scanning comes in.
Why Automation Matters
Automated vulnerability scanners can monitor your environment constantly, flagging new vulnerabilities as they appear. They’re fast, consistent, and cost-effective.
That doesn’t mean you ditch human-led testing. Tools can’t always catch the nuanced logic flaws or chained exploits that skilled testers can uncover.
The Smart Approach: Combine Both
The best strategy we’ve seen is combining ongoing vulnerability scanning with periodic, manual penetration testing. It gives you:
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Continuous coverage for fast-moving threats
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Deeper insights from human testers
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A budget-friendly balance between automation and expertise
Picking the right penetration testing company goes beyond technical skills. You need a partner who gets your business, understands your compliance needs, and supports your long-term security strategy. A strong testing partner can help you prioritize risk, allocate resources effectively, and stay audit-ready throughout the year.
Final Thoughts: Build a Testing Strategy That Works for You
If you’re still wondering how often penetration testing should happen, here’s the honest answer: often enough to stay ahead of risks, but in a way that makes sense for your business.
Start with the requirements of your relevant frameworks. Then, assess your risk, change cadence, and resource availability. From there, develop a testing strategy that combines the strengths of both continuous and periodic assessments.
And remember: the right partner can make all the difference. Partnering with skilled penetration testing companies helps you meet SOC 2, ISO 27001, HIPAA, PCI-DSS, or FedRAMP goals. This support boosts compliance and enhances long-term security maturity.
Need help figuring out where to start? Trava helps companies of all sizes create smart, sustainable security compliance testing strategies. And we’d love to help you too. Reach out today!