How Often Should You Conduct a Penetration Test?

It's safe to say that cybersecurity is no longer a technical concern reserved for the IT department, it is a board-level issue that defines whether or not you get 'breached' or not.

In 2025, The penetration test is still one of the most powerful tools in your cybersecurity toolkit. But how often should you conduct one? That question usually reveals more profound confusion about risk management, compliance requirements, and security maturity.

This blog explores the optimal frequency for penetration testing based on industry best practices, business size, and operational risk. It also outlines how UK organisations can embed a testing cadence that supports compliance, protects assets, and demonstrates due diligence to stakeholders.

The threat landscape is dynamic. New vulnerabilities emerge daily, systems change frequently, and the attack surface expands with every product launch, software update, or staff turnover. Conducting a one-time penetration test might reveal issues, but without regular follow-up, those gaps can resurface or multiply unnoticed.

A consistent testing schedule ensures your organisation’s defences keep pace with change. It supports a proactive approach to security, where weaknesses are identified before adversaries have the chance to exploit them.

For Managing Directors of UK SMEs and IT leaders in larger firms alike, understanding the right cadence helps avoid over-testing (wasting resources) or under-testing (leaving blind spots).

How Often Should You Conduct Cybersecurity Testing?

When it comes to cybersecurity, regular testing is essential for maintaining robust defences against ever-evolving threats. Various industry standards and frameworks provide useful guidance on how frequently organisations should test their systems, but it is crucial to remember that these serve as a baseline rather than a complete solution. Understanding these standards and going beyond them is key to developing a resilient cybersecurity posture.

Standards and Regulatory Expectations

Several widely recognised standards set the minimum expectations for cybersecurity testing. For instance, ISO/IEC 27001, a leading information security management standard, recommends conducting security testing whenever there are significant changes to systems or infrastructure. This ensures that any new vulnerabilities introduced through updates or modifications are promptly identified and addressed.

The Payment Card Industry Data Security Standard (PCI DSS) is more specific in its requirements. It mandates penetration testing at least once a year and after any substantial system change. This standard is particularly relevant for organisations handling payment card data, as breaches in this area can lead to severe financial and reputational damage.

In the UK, the Network and Information Systems (NIS) Regulations apply to operators of essential services and digital service providers. These regulations mandate regular assessments of network and information systems security, with the aim of improving resilience across sectors that are critical to national infrastructure.

Cyber Essentials Plus, a UK government-backed scheme, requires vulnerability scanning as a baseline. It also encourages additional testing based on the organisation's risk profile. While it offers a good starting point, Cyber Essentials Plus should ideally be part of a broader, layered security strategy.

For those in the financial sector, the Financial Conduct Authority (FCA) expects regulated institutions to perform regular cybersecurity testing. This ensures that firms are adequately protecting consumer data and maintaining trust in the financial system.

Beyond Minimum Requirements: Tailored Testing Strategies

While these standards offer valuable guidance, best practice involves tailoring testing frequency to your organisation’s unique risk profile and operational tempo. A business that frequently updates its infrastructure or handles sensitive data may require more frequent assessments than one with relatively static systems and low-risk operations.

Conducting risk assessments can help determine the most appropriate testing schedule. For example, organisations facing a high likelihood of targeted attacks such as those in finance, healthcare or government should consider more frequent penetration testing and continuous monitoring solutions. Similarly, companies undergoing rapid digital transformation should treat every major deployment or integration as a trigger for fresh security testing.

Ultimately, cybersecurity testing should be proactive rather than reactive. Waiting for an annual deadline or a significant change before testing can leave gaps that threat actors may exploit. By embedding security testing into the fabric of your organisation’s operations, you not only meet regulatory expectations but also significantly reduce your exposure to cyber threats.

While standards like ISO/IEC 27001, PCI DSS, NIS Regulations, Cyber Essentials Plus and FCA guidance provide a strong foundation, truly effective cybersecurity relies on a risk-based approach. Regular, tailored testing aligned with your business needs will help ensure your systems remain secure in an ever-changing threat landscape.

Why Risk Should Drive Your Penetration Testing Frequency

When it comes to determining how often penetration testing should take place, there is no one-size-fits-all answer. The most effective approach is one that aligns with your organisation’s specific risk profile. High-risk environments inevitably demand more frequent and thorough assessments, while lower-risk settings may get by with less frequent reviews. The key is understanding what constitutes risk in your context and adapting your testing schedule accordingly.

Factors That Influence Testing Frequency

Several variables play a critical role in determining the right testing cadence. One of the most important is business size and sector. High-profile organisations such as financial services firms, healthcare providers and critical infrastructure operators are often prime targets for cyberattacks. These sectors handle sensitive data and deliver essential services, making them attractive to malicious actors. As such, they may benefit from quarterly or even monthly penetration testing. On the other hand, small to medium-sized enterprises (SMEs) with less exposure might find that biannual or annual testing is sufficient.

Another vital factor is data sensitivity. The more sensitive the information you hold such as personal customer records, payment details, or intellectual property the greater the incentive for threat actors to target your systems. Regular testing helps to identify and patch vulnerabilities before they can be exploited, providing an added layer of defence for your most valuable assets.

Regulatory requirements also significantly influence how often testing should occur. Organisations operating under strict compliance frameworks such as GDPR, PCI DSS or HIPAA may be required to conduct regular assessments to maintain their certifications and avoid penalties. In these cases, failing to test frequently enough can have legal and financial consequences.

Changes to your systems are another trigger for renewed testing. Whenever your infrastructure undergoes modifications such as a cloud migration, an application update, or the integration of a new API it’s essential to assess for any new vulnerabilities that may have been introduced. Ignoring this step can leave security gaps that attackers could exploit.

Finally, your incident history matters. If your organisation has suffered a breach or security incident, it’s a clear signal that your existing controls may be insufficient. In such scenarios, increasing the frequency and depth of your testing can help regain control and rebuild trust.

Testing with Cybergen

At Cybergen, we specialise in helping organisations create dynamic, tailored penetration testing schedules. We understand that risk is not static—it evolves with your business, your technology, and the wider threat landscape. That’s why we advocate for flexible, risk-informed testing strategies.

There is no universal rule dictating how often penetration testing should occur. Instead, the best results come from intelligent planning rooted in a clear understanding of your unique risk posture. By aligning your security testing with actual business needs, you can ensure the efficient use of resources while maintaining strong protection against cyber threats.

Embedding Penetration Testing into Agile and DevOps Workflows

In today’s fast-paced development environments, traditional annual penetration testing is rapidly becoming outdated. Agile and DevOps methodologies encourage frequent code releases, which can inadvertently introduce new vulnerabilities at a much faster rate. Waiting an entire year to uncover these issues simply doesn’t align with the speed and scale of modern software delivery.

To address this challenge, forward-thinking organisations are embedding security testing directly into their CI/CD (Continuous Integration/Continuous Deployment) pipelines. This approach ensures that penetration testing evolves alongside the application lifecycle, providing continuous visibility into potential weaknesses as new features are built and deployed.

This is where the concept of Continuous Penetration Testing, also known as Penetration Testing as a Service (PTaaS), comes into play. Unlike traditional point-in-time assessments, PTaaS offers an ongoing security evaluation model, allowing teams to detect and respond to threats in real time.

Balancing Budget and Security: Making Penetration Testing Affordable

One of the most common objections to increasing the frequency of penetration testing is budget. It’s understandable—regular testing involves costs, and for many organisations, resources are limited. However, it’s important to consider the bigger picture. The financial impact of a cyberattack ranging from regulatory fines and lost customer trust to downtime and recovery expenses can far exceed the cost of proactive security testing.

In this context, investing in regular assessments is not just a cost but a safeguard against potentially catastrophic losses. Rather than viewing penetration testing as a one-off expense, it should be seen as part of a continuous risk management strategy.

Fortunately, budget constraints don’t mean you have to choose between security and affordability. A staggered testing approach offers a practical middle ground. Instead of testing every asset each time, organisations can rotate their focus. One quarter could be dedicated to web applications, the next to infrastructure, followed by cloud environments or APIs. This rotation keeps testing relevant and timely while spreading costs more evenly throughout the year.

At Cybergen, we work with clients to create tailored testing plans that align not only with their risk profile but also with their financial realities. Our goal is to make effective security accessible—helping organisations maintain visibility across their digital estate without overextending their budgets.

By taking a strategic and flexible approach, businesses can ensure that security remains a priority, even when resources are limited.

Penetration Testing for UK SMEs: Why It Matters

Small and medium-sized enterprises (SMEs) often wonder whether they need to test their security as frequently as larger organisations. The simple answer is: not necessarily. However, that doesn’t mean testing can be ignored. In fact, SMEs are often seen as prime targets by cybercriminals because they’re less likely to invest in robust security measures including penetration testing.

Cyberattacks don’t discriminate by company size. A successful breach can lead to lost data, damaged customer trust, and significant financial consequences. That’s why establishing a strong baseline of security testing is essential for any SME looking to protect its operations and reputation.

For most UK SMEs, annual penetration testing, when paired with monthly vulnerability scans, offers a practical and effective security foundation. This approach provides regular visibility into potential weaknesses while keeping costs manageable. If your business handles sensitive customer information such as personal data, payment details, or proprietary content you may need to test more frequently or conduct additional assessments following system changes, software updates, or infrastructure upgrades.

At Cybergen, we understand the unique challenges faced by SMEs. That’s why we offer scaled-down, high-impact penetration tests designed specifically for smaller businesses. Our services strike a balance between cost and coverage, ensuring that you get the insights you need without overstretching your budget.

Cybersecurity isn’t just for big enterprises. With the right strategy, SMEs can build strong, resilient defences starting with smart, regular testing.

Building a Penetration Testing Calendar: A Practical Guide for IT Leaders

For CTOs, CISOs and IT managers, a structured penetration testing calendar is more than just a schedule—it’s a strategic tool for ensuring accountability and maintaining security posture throughout the year. Rather than taking a reactive approach, planning in advance brings visibility, efficiency and alignment with business priorities.

Here’s how to build an effective testing calendar:

Map Your Environment: Begin by listing all critical systems, applications and data flows. Understanding the landscape is essential to ensure nothing important is missed.

Assess Change Frequency: Identify how often these assets undergo changes, such as software updates, infrastructure upgrades or configuration adjustments. Systems that change frequently are more likely to introduce new vulnerabilities.

Define Risk Levels: Evaluate each asset’s sensitivity, accessibility, and potential business impact. High-risk assets should be prioritised for more frequent testing.

Align with Compliance: Incorporate any mandatory testing timelines based on relevant regulatory requirements. These may include standards like ISO 27001, PCI DSS or Cyber Essentials Plus.

Plan by Quarter: Spread your testing activities across the year to manage resource use and avoid bottlenecks. For instance, focus on applications in Q1, infrastructure in Q2, and cloud services in Q3.

At Cybergen, we help clients bring this process to life through planning workshops and custom calendar templates. These tools simplify the process, allowing IT leaders to establish a consistent and risk-based testing cadence that supports ongoing security and compliance.

Penetration testing should not be a checkbox exercise. The value lies in what you do with the results. After each test, a review cycle should follow:

Debrief with stakeholders: Technical and executive audiences.
Remediation planning: Assign responsibilities and timelines.
Risk reassessment: Update risk register.
Track progress: Review in subsequent tests.

Cybergen’s reports are designed to support these cycles. Each one includes risk ratings, remediation advice, and executive summaries that drive strategic conversations.

When External Factors Trigger Penetration Testing

While many organisations plan their penetration testing around internal development cycles or risk assessments, external factors can often dictate the timing. In some cases, you may find that testing is not driven by your internal calendar but by external pressures that demand swift action and documentation.

One common driver is client demand. Large enterprise clients frequently require security assurances before onboarding new suppliers or renewing contracts. A recent penetration test can be a prerequisite, demonstrating your organisation’s commitment to security and reliability.

Cyber insurance providers are also tightening requirements. Increasingly, insurers are asking for proof of regular security assessments—including penetration testing as a condition of coverage or to secure more favourable terms. Failing to meet these expectations could impact your eligibility or premiums.

Regulatory changes are another key trigger. New legislation or industry-specific compliance updates may require updated testing or more frequent assessments. Similarly, audits whether internal or external—often uncover gaps that must be addressed through formal testing.

Finally, public incidents can serve as a wake-up call. A high-profile breach in your industry may prompt leadership or stakeholders to request an immediate review of your own security posture.

Having a clear, well-documented testing schedule in place not only supports internal readiness but also signals governance maturity to clients, partners, and regulators. At Cybergen, we help organisations stay prepared—whether tests are planned proactively or required reactively.

Cybergen provides CREST-accredited penetration testing to UK organisations across sectors. We help clients develop intelligent, risk-based testing schedules, aligned with compliance, operational need, and business strategy.

Our services include:

Annual and quarterly penetration testing packages
Penetration Testing as a Service (PTaaS)
On-demand assessments following system changes
Reporting tailored to technical and executive stakeholders
Remediation workshops

Our goal is not just to find vulnerabilities, but to help you manage them effectively over time.

Penetration testing is not just a technical task it is a strategic activity that protects your organisation’s future. Testing once and assuming you're secure is no longer viable. Threats evolve, your systems change, and attackers are always looking for the next gap.

By adopting a regular testing cadence based on your business model, risk tolerance, and compliance requirements you stay ahead of threats and demonstrate due diligence to stakeholders.

For UK SMEs, annual testing may suffice. For regulated or high-risk businesses, more frequent testing is essential. Cybergen stands ready to help you determine what works best, deliver testing when it matters, and transform results into lasting resilience.

Because in cybersecurity, timing isn’t everything, it’s the only thing.