Penetration Testing for Regulatory Compliance

Penetration testing is one of the most effective ways to know if your security really works. Instead of waiting for a real cyberattack to happen, you hire an “ethical hacker” to try to break your defenses and tell you where they could get in. It’s that simple. This kind of test not only helps you understand your risks, it also gives you the chance to fix them before it’s too late.

That’s why most major compliance frameworks (like PCI DSS, ISO 27001, or SOC 2) don’t just recommend penetration testing—they often require it. Even when they don’t literally spell it out, the requirements are written in such a way that, to truly comply, you need a proper pentest. In short, if your goal is to be aligned with regulations, penetration testing is not optional—it’s part of the game.

Why is penetration testing essential for regulatory compliance?

Today, organizations face a dual pressure: protecting their digital assets and proving compliance with global regulatory requirements. Penetration testing (pentesting) has become an essential tool for both, especially when the goal is to align cybersecurity with compliance.

A penetration test goes far beyond a technical check. It’s an organized, realistic way to put your defenses to the test and see if they actually hold up against an attack. In compliance terms, that kind of verification is gold: it provides concrete evidence you can show to auditors, regulators, or even your own clients.

Pentesting for regulatory compliance serves three main purposes:

1. Demonstrating due diligence to regulators by validating that active measures have been taken to prevent unauthorized access.

2. Identifying security gaps before they are exploited, which is key in regulations that require proactive risk management.

3. Documenting and mitigating vulnerabilities as part of a continuous improvement cycle in the organization’s cybersecurity strategy.

In addition, many regulations explicitly require periodic penetration testing, especially when significant changes are made to infrastructure, applications, or internal processes. This approach helps prevent complacency and fosters a security culture built on continuous improvement.

Which regulations require or recommend pentesting?

If you work in cybersecurity or compliance, you know that many major regulations either include (or strongly imply) that you should be doing penetration tests. Some state it directly, others leave it between the lines. Here’s a rundown of the most important frameworks:

1. PCI DSS (Payment Card Industry Data Security Standard): One of the clearest. Requirement 11.3 states that you must perform internal and external penetration tests at least once a year or after significant infrastructure changes. The goal? Ensuring payment card data is well protected. It also requires that tests follow recognized standards like NIST SP 800-115.

2. ISO 27001: Does not explicitly require pentesting, but it does require risk assessments and continuous control verification. In practice, conducting a solid pentest is the most direct way to validate that your security management system is doing its job. Highly recommended.

3. SOC 2: Especially in Type II, SOC 2 focuses on how your security controls perform over time. A well-executed pentest gives you strong evidence that those controls hold up under pressure. Companies handling third-party data often rely on these tests to demonstrate real compliance.

4. HIPAA: While this U.S. healthcare regulation doesn’t mandate pentesting per se, it does require continuous risk assessments and “reasonable” safeguards. In this context, penetration testing is an effective way to meet those requirements and avoid potential penalties.

5. GDPR: The European regulation doesn’t use the word “pentesting,” but it does require you to ensure an “appropriate level of security” (Article 32). Penetration testing is one of the best ways to prove you take personal data protection seriously.

6. SWIFT CSP: If your company operates with the SWIFT system, pentesting is not optional. This cybersecurity framework requires independent testing of critical infrastructure. Here, penetration tests are fundamental to validating that financial systems are truly secure.

Read more: Why Pentesting Is Key in a Cybersecurity Strategy

Pentesting Modalities for Compliance: Which One Do You Really Need?

When it comes to meeting regulatory requirements, it’s not enough to just run “any pentest.” Not all tests are created equal, and how you conduct them can make the difference between achieving compliance—or falling short. Here are the main modalities and why you should pay close attention to them.

Manual vs. Automated: People or Machines?

1. Automated Pentesting: These tests rely on tools that scan your infrastructure for known vulnerabilities. They’re fast, cost-effective, and do the job well when you need frequent reviews or to meet periodic scanning requirements. But beware: their scope is limited.

2. Manual Pentesting: This is where real ethical hackers come in. They simulate realistic attacks, looking for creative combinations of errors, unauthorized access, and weaknesses in business logic. The result? A much deeper and more realistic assessment. When it comes to serious audits or strict regulations, manual tests usually carry more weight and credibility.

Internal vs. External: From the Inside or Outside

1. Internal Pentesting: Imagine an attacker has already gained access to your network (for example, a malicious insider or someone who slipped in through a previous breach). These tests evaluate how easy it would be to move laterally within your system and reach sensitive information.
   
   
2. External Pentesting: Simulates what a cybercriminal would do from the Internet. It tests your firewalls, exposed servers, and any asset visible from the outside. It’s ideal for understanding how you look (and how vulnerable you are) from an attacker’s perspective. The best approach—especially under frameworks like PCI DSS—is to combine both. Only then do you get a complete picture of your security posture.

PTaaS: Pentesting as a Service

This modern approach combines the best of both worlds: in-depth technical testing plus a cloud-based platform where you can see results in real time, manage findings, and collaborate with your security team.

Key Advantages of PTaaS:

1. Immediate results—no need to wait weeks for a final report.

2. Integration with your DevSecOps tools.

3. Faster response and remediation times.

4. Flexibility to run tests more frequently.

PTaaS doesn’t completely replace traditional approaches, but if you’re looking for agility without sacrificing regulatory compliance, it’s an option well worth serious consideration.

How to Define the Scope and Frequency of Pentesting

One of the most common mistakes companies make is conducting pentests just to tick off a compliance checklist—without considering what’s being tested, how often, or whether it actually covers their most relevant risks. The result? Useless reports, critical blind spots, and half-baked compliance.

Where to Start? Define the Scope Properly

The scope of a pentest can’t be random. It must be aligned with what truly matters to your business and the requirements of the regulations that apply to you. Key points to include:

1. Critical Assets: Systems, applications, and services that handle sensitive data or key functions. If something goes down or gets compromised, what would the impact be? That goes in the scope.

2. Specific Regulatory Requirements: Some frameworks like PCI DSS are very explicit about what needs to be tested (e.g., network segmentation, systems processing card data).

3. Recent Changes: If you updated your infrastructure, migrated to the cloud, or launched a new app, all of that should be included.

The goal is for pentesting not to be just a snapshot in time, but a realistic assessment of your risk level and exposure.

How Often Should You Run Pentests?

It depends on the compliance framework you follow—but also on how dynamic your business environment is. Here are some practical examples:

1. PCI DSS: At least once a year and after any significant changes to your environment.

2. ISO 27001, SOC 2, GDPR: At least once a year. If you operate in a fast-moving environment, do it more frequently.

3. HIPAA and SWIFT CSP: No exact number given, but they require proof of continuous risk monitoring.

Do you work in an agile or DevOps environment? In that case, the best practice is to move toward continuous pentesting—combining frequent automated scans with periodic manual validations. That way, you catch vulnerabilities as early as possible without sacrificing compliance

Read more: What is retesting in penetration testing (pentests)?

How to Measure if a Pentest Really Helps You Comply

A pentest isn’t just about finding flaws. It’s about understanding how well your defenses are working, whether your teams are prepared to respond, and—most importantly—whether you’re aligned with regulatory requirements.

To know if a pentest was effective (and useful from a compliance perspective), there are certain metrics you can’t skip.

1. What Did You Find, and How Severe Was It?

It’s not just about counting vulnerabilities. The key is classifying them properly: low, medium, high, or critical. Using a system like CVSS helps you speak the same language as auditors and regulators. What really matters is how quickly and effectively you handle the most critical findings.

2. MTTR: How Long Did It Take to Fix?

The well-known Mean Time to Remediate (MTTR) measures the average time it takes you to resolve a vulnerability. From a compliance standpoint, this matters just as much as detecting the issue in the first place. The lower your MTTR, the more mature your response process.

3. False Positives: Less Is More

Are you spending days analyzing issues that turn out not to be problems? That’s a red flag. A good pentest should minimize false positives. More noise means less focus.

4. How Complete Was It?

Coverage is critical. Did the pentest address your most important systems? Applications handling sensitive data? Endpoints with privileged access? If the most critical assets weren’t tested, you’re leaving doors open without realizing it.

5. Maturity Level: How Are You Evolving?

Common Mistakes (and How to Avoid Them)

Yes, pentesting offers many advantages—but there are also pitfalls that companies fall into again and again. Some of the most common are:

1. Treating it as a formality: Running a test just to tick the box, without integrating it into the security cycle or DevSecOps.

2. Unclear technical reports: Filled with jargon, lacking actionable steps.

3. Not tying it to compliance requirements: Generic tests that don’t meet what specific standards demand.

4. Ignoring the results: Due to lack of resources, time, or simply willingness to remediate.

Read more: Common Mistakes in Penetration Testing and How to Avoid Them

Best Practices That Really Work

To make pentesting worthwhile and truly support compliance, keep these in mind:

1. Document everything properly: dates, findings, responsible parties, and remediation actions.

2. Integrate it into the development cycle: don’t wait until the end—test earlier.

3. Use compliance checklists: to make sure nothing critical slips through.

4. Train technical teams: so they know how to read the report and act quickly.

5. Cross perspectives: involve IT, legal, compliance, and cybersecurity. Everyone has something valuable to contribute.

When you apply these practices, you not only strengthen your security posture—you also gain credibility (and peace of mind) with auditors, clients, and partners.

Conclusion: Meeting Compliance with Pentesting Doesn’t Have to Be a Headache