Continuous Penetration Testing: How to Mature Your Approach | Kroll

Cyber

January 9, 2026

Continuous Penetration Testing: How to Mature Your Approach to Assessments

As cyber threats grow more sophisticated and persistent, traditional penetration testing methods, often conducted quarterly or annually, can miss key vulnerabilities and lack coverage. Continuous penetration testing enables organizations to identify and remediate vulnerabilities in real time, providing product and software teams with up-to-date insight and evidence to advance security and enhance regulatory compliance. This article sets out the security advantages delivered by continuous penetration testing, the ways in which this type of pen testing complements existing assessment approaches, and the first steps organizations can take to mature their security assessment strategy.

What is Continuous Pen Testing?

With technical environments constantly changing and new types of vulnerabilities continually emerging, periodic pen testing only provides a one-off perspective on the status of a company’s application or network. Continuous pen testing is an advanced type of security framework through which an organization's digital assets are tested on an ongoing basis, helping to identify and address security vulnerabilities more proactively. This type of assessment complements the insight provided by periodic pen testing because it delivers real-time insight into potential vulnerabilities introduced by the product and software engineering process. While automation forms a significant element of continuous pen testing, it also involves manual interventions by pen testing specialists.

By leveraging continuous pen testing alongside annual pen testing, companies can more effectively identify, exploit and eliminate weaknesses in their software and web applications.

How Does Continuous Pen Testing Work?

The continuous pen testing process usually involves the following steps:

Manual Testing
A baseline of an organization’s attack surface and assets is first gained through a full manual penetration test. This tests all external digital assets, leveraging penetration testing approaches and methodologies, such as those from OWASP, NIST and MITRE ATT&CK. Continuous penetration testing begins in the same way as traditional testing: with a full assessment. Unlike a traditional test, it does not stop there because that first assessment instead forms a baseline.
Continuous Pen Testing Cycle
A cycle of continuous pen testing is then undertaken. This should include identifying assets, defining scope and expectations, the testing process itself, remediation, retesting and validation and tracking new vulnerabilities.
Cycle Repeated
The cycle is then completed again. Alongside checking for changes caused by new types of security issues, the system monitors existing results for vulnerabilities that then require testing.

Continuous Pen Testing and Agile Pen Testing

Agile pen testing is a continuous security assessment approach that allows software teams to accelerate the pace of delivering secure software to their customers. Continuous pen testing and agile pen testing are two sides of the same coin, with both providing the scope to test continuously and assess application stacks consistently, as well as the ability to leverage both manual and automated techniques. However, there are some critical differences which shape how and when organizations leverage them.

Continuous Pen Testing and Agile Pen Testing: Key Differences

Continuous Pen Testing	Agile Pen Testing
This type of pen testing is led and managed by service provider.	Agile pen testing is a collaborative process between provider and client organization.
The pen testing provider has ownership of this type of assessment.	The eventual ownership of this type of assessment framework is with the client company.
Because the external provider takes the lead on the assessments, there is very heavy lifting on the execution side by the client company.	This type of assessment will usually involve changes to an organization’s internal team.
This form of assessment is a focused exercise, usually with minimal internal costs.	Because this is an approach to actively help transform an organization’s security practice it will involve a nominal effort from internal teams. On the bright side, this will extend and fully utilize the capabilities of internal tooling and infrastructure.
Continuous pen testing is suitable for most types of organizations or scope of assessments.	Agile pen testing is best suited for organizations that have an internal security team or those that would like to increase internal security checkpoints in addition to external validation.

Download the Kroll eBook, An Introduction to Agile Pen Testing

Continuous Pen Testing and Periodic Pen Testing: The Best of Both Worlds

Continuous Pen Testing vs Periodic Pen Testing

	Traditional Pen Testing	Continuous Pen Testing
Approach	Periodic	Ongoing process and/or triggered by change
Level of Insight	Snapshot of a specific point in time	Real-time visibility of vulnerabilities as they occur
Depth of Testing	High	High
Automation	Low on automation, high on human-led investigations	Leverages a range of automated tools to accelerate testing, but includes validation by experts where appropriate
Flexibility	Fixed Scope	Dynamic scope

Adopting an either-or approach to continuous and traditional pen testing is not beneficial for organizations. Combining the best of both options ensures that software teams reap the rewards of a more holistic approach. Continuous pen testing complements and enhances the security advantages provided by traditional pen testing. This is particularly important with the security landscape shifting so quickly due to changes such as threat actors leveraging AI for attacks and the rise of geopolitical tensions. As a result, it is vital that organizations regularly review and update their security assessment program and software engineering process.

While annual pen testing remains a vital aspect of an effective security posture, continuous pen testing provides another layer of security. Organizations should analyze and improve how they leverage pen testing with a strategy that combines both types of testing.

Common Use Cases: When to Leverage Continuous Pen Testing

While continuous pen testing offers a range of benefits, it is particularly advantageous for certain scenarios and types of organizations, including:

Fast-Moving IT Environments	Compliance-Heavy Industries	Enhancing Software Development
Continuous penetration testing can be highly beneficial for organizations with dynamic and complex IT environments that involve product and software engineering. Companies that frequently introduce new web and mobile applications, updates or services, will benefit from ongoing testing as this lowers the potential for overlooked vulnerabilities to be exploited by threat actors.	Organizations in industries in which regulatory and compliance requirements are particularly rigorous , gain a significant advantage from continuous pen testing as it provides up-to-date evidence of proactive testing.	Continuous penetration testing supports better software development by enabling frequent testing and remediation, helping developers understand secure development practices and prepare to incorporate them into their work. Adopting a continuous model provides valuable proof to clients that every version of a piece of software has been thoroughly assessed.

Implementing Continuous Penetration Testing: Next Steps

Looking to mature your organization’s approach to security assessments through continuous pen testing? These are the essential first steps in that journey:

Scope Out Your Business Objectives and Attack Surface

Our LLM security methodology is continually updated to reflect new changes in this fast-evolving area of security. We offer a detailed approach to ensure that our team covers all key areas when completing an LLM security assessment.

Choose Your Methodology

This stage involves identifying which testing approaches are best for specific assets. Types of methodologies used include partially closed-box penetration testing, in which only limited information is shared with the tester, open-box penetration testing, which involves sharing full network and system information with the tester, and closed-box penetration testing, in which no information is provided to the tester at all. Partially closed-box is often considered the most appropriate choice because it provides a good balance between depth and efficiency.

Select Your Partner and/or Platform

Deciding on which continuous pen testing partner to work with calls for careful consideration of your prospective partners’ level of experience, expertise and of course, the scope of their technology and how effectively this can integrate with your organization’s tools. Ask about their breadth of experience in security assessments, how they support hybrid environments, and how they balance automation with validation by experts. From there, your chosen provider should undertake the first penetration test to set out a baseline for your organization’s security and uncover existing vulnerabilities.

Leveraging the Advantages of Continuous Penetration Testing

In today’s fast-moving threat landscape, it is critical to ensure real-time visibility of vulnerabilities and the ongoing ability to mitigate them. Continuous penetration testing enables organizations to achieve this and more. Threat actor tactics are evolving, as are regulatory and compliance requirements across many industries. By leveraging continuous penetration testing, businesses can benefit from high quality security insights and evidence and easier alignment with regulations.

When considering the advantages of continuous pen testing, cyber security leaders and decision-makers should avoid seeing annual pen testing and continuous pen testing as an either/or decision but instead look at how these and other types of assessments can contribute to a mature security posture throughout the product and software engineering process.

With organizational attack surfaces diversifying in complexity, continuous pen testing, complemented by annual pen testing, is set to play a central role in mature cyber security strategies. Organizations should aim to identify a security partner with the proven level of insight and expertise to ensure they can maximize the impact of continuous penetration testing.

The ‘How’ of Continuous Pen Testing: Breadth vs Depth

Kroll’s approach to continuous pen testing is geared toward enabling software and app development teams to achieve scale or horizontal breadth in terms of constantly evolving large applications that are different every time they are tested. One example is software product companies releasing something new within their app every three months. Because the application is constantly growing in size, continuous pen testing is required to continually assess for issues. The other type of pen testing is where the application changes more in terms of complexity and depth, also requiring continuous pen testing. At Kroll, we have developed a pen testing methodology to support clients that need to consistently and frequently test applications due to either of these two business needs. This contrasting approach between testing breadth and testing depth is outlined below.

Typical Client Type 1: Large enterprises, banks, financial institutions, insurance companies, retail organizations

Software Type: These companies’ applications don't change very often, but are very high volume, for example, 500 to 1000 applications requiring testing once or twice a year.

Testing Focus: Testing at breadth

Typical Client Organization Type 2: Major companies

Software Type: These businesses have one single application, but with frequently added new features which means the application is growing vertically.

Testing Focus: Testing at depth

Advance Your Pen Testing Strategy with Kroll

Kroll’s sophisticated and scalable approach to penetration testing is defined by our combination of front-line threat intelligence, thousands of hours of cyber security assessments completed each year and a global team of highly certified cyber experts.

Kroll performs testing to the highest technical, legal and ethical standards. Our award-winning pen test services include complete post-test care, actionable outputs, prioritized remediation guidance and strategic security advice to help you make long-term improvements to your cybersecurity posture. Insights from our world-class incident response practice directly feed our certified cyber experts the information they need to test against the exploits that attackers are executing right now.

With proven experience of working as an extension of clients’ security teams, our collaborative approach sets us apart. We work with software development and product engineering teams across many industries. As a business, we have the scope and experience to ensure that a growing enterprise’s continuous penetration testing program runs on time and on budget. Kroll clients can package pen testing and other assessment services as part of Kroll’s Enterprise Risk Retainer, which helps organizations stay ahead of emerging risks with proactive risk management, financial predictability and expert-led incident response services.

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Connect with Us

Rahul Raghavan

DirectorCyber and Data ResilienceToronto

Rahul Raghavan [email protected]

Krishna Raja

Managing DirectorCyber and Data ResilienceToronto

Krishna Raja [email protected]+1 4166433506

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