Beyond Snapshots: The Need For Continuous Penetration Testing

By James Rees, MD, Razorthorn Security

Times must change (and always will) and nowhere is this more true than in the realm of technological advancement. Thirty years ago, the technological landscape was vastly different from what we have today and technological change has outpaced Moore’s Law for some time now. Information security must keep pace with these advancements. This has become especially true with the advent of AI.

Penetration testing has been a standard requirement for many years. All major legislative and compliance frameworks, such as PCI DSS and ISO 27001, have mandated penetration testing at least annually or after any significant change. While this has been the status quo, the rise in data breaches, along with the introduction of more stringent legislation and enhanced cybersecurity frameworks, has led to increased calls for more robust security measures. Many cybersecurity professionals are now advocating for continuous penetration testing as a powerful tool in their arsenal for managing threats and assessing vulnerabilities.

Continuous penetration testing refers to the process of conducting penetration tests on an ongoing basis, as opposed to the traditional periodic model. This approach is designed to identify vulnerabilities and weaknesses continuously, rather than just once a year or after significant changes to the system.

The 3 key reasons why continuous penetration testing is gaining traction

1. We need to keep pace with cyber threats

The speed of technological advancements means that new vulnerabilities can emerge at any time. The traditional model of annual or post change penetration testing risks missing these vulnerabilities, leaving organisations exposed for potentially long periods.

2. Delaying can cost you

The increasing sophistication of cyber threats necessitates that organisations stay ahead of attackers. Cybercriminals now use advanced techniques and automation to relentlessly target systems and networks. In this environment, waiting for an annual penetration test could prove to be too late.

3. Remain compliant

the regulatory landscape has become more stringent in many regions worldwide, increasing the need for organisations to demonstrate due diligence in managing cybersecurity risks. Continuous penetration testing can serve as evidence that an organisation is taking a proactive approach to cybersecurity.

Continuous penetration testing offers several advantages over traditional methods. It enables real time identification and remediation of vulnerabilities, significantly reducing the window of opportunity for attackers. It also provides a clearer and more up to date picture of an organisation’s security posture, rather than relying on assessments at set intervals.

However, implementing continuous penetration testing requires careful planning and resources. Organisations must have the right tools for continuous monitoring and assessment of their networks and systems. Additionally, skilled professionals are required to interpret test results accurately and respond effectively.

Let’s take a look at continuous penetration testing in more detail.

The Evolution of Penetration Testing: From Periodic to Continuous

Historically, penetration testing has been a periodic exercise conducted annually, biannually, or quarterly. These tests simulated attacks on systems, networks or web applications to identify vulnerabilities that could be exploited by cybercriminals. However, traditional penetration tests only provided a “snapshot” of an organisation’s security posture at a single point in time and this approach had significant limitations.

Periodic penetration testing often led to a false sense of security. Once tests were completed, organisations assumed their systems were secure until the next scheduled test. However, as we know, cybersecurity threats evolve constantly. New vulnerabilities are discovered regularly and attackers continuously develop new tactics. The static approach of periodic testing has proven inadequate for maintaining a strong security posture in this dynamic threat landscape.

Continuous penetration testing emerged to address these limitations. This approach involves ongoing, automated testing of an organisation’s infrastructure, applications and systems to identify vulnerabilities in real time. Instead of testing at fixed intervals, continuous penetration testing provides ongoing assessments, enabling organisations to detect and respond to vulnerabilities as soon as they arise.

Benefits of Continuous Penetration Testing

The shift from periodic penetration testing to continuous penetration testing offers several significant benefits:

1. Real Time Vulnerability Identification and Remediation

In cybersecurity, time is critical. Continuous penetration testing enables organisations to detect vulnerabilities as they emerge, rather than waiting for the next scheduled test. This real time insight allows security teams to remediate vulnerabilities before they can be exploited by threat actors. This is particularly important in dynamic environments where new code, configurations and systems are frequently deployed.

2. Improved Security Posture

Continuous penetration testing offers a more accurate and comprehensive view of an organisation’s security posture. Instead of a one off snapshot, security teams gain continuous visibility into the evolving threat landscape. This enables organisations to respond quickly to changes in their environment and adapt to new attack vectors more effectively. By continuously testing their systems, organisations can address weaknesses proactively, reducing the risk of successful cyberattacks and improving overall security.

3. Greater Compliance with Regulatory Requirements

As regulatory frameworks evolve, continuous penetration testing is becoming a key requirement for compliance. Regulatory bodies increasingly recognise the need for ongoing assessments to ensure robust cybersecurity practices. Regulations such as GDPR, PCI DSS and the Digital Operational Resilience Act (DORA) in the EU emphasise continuous testing and monitoring.

For instance, PCI DSS requires regular testing of systems and networks to ensure compliance with security standards. While traditional penetration testing was once sufficient, continuous testing is now viewed as a more effective way to maintain compliance.

4. Enhanced Coverage of Complex IT Environments

Modern IT environments are complex and dynamic, often encompassing on premises infrastructure, cloud environments, web applications and mobile platforms. The increasing reliance on cloud services, including Platform-as-a-Service (PaaS) and Software-as-a-Service (SaaS), introduces additional complexity.

Continuous penetration testing is well suited to these environments, providing continuous coverage across all aspects of an organisation’s IT ecosystem. This comprehensive approach ensures that vulnerabilities are identified and remediated across the entire infrastructure, regardless of their location.

5. Cost Efficiency Over Time

While the initial implementation of continuous penetration testing may require a larger investment than traditional testing, it tends to be more cost effective in the long run. Continuous testing automates many of the manual processes involved in traditional penetration testing, reducing the need for frequent manual assessments. Additionally, by identifying and remediating vulnerabilities in real time, organisations can prevent costly data breaches and minimise the financial impact of cyber attacks.

The Trend Towards Continuous Testing in Compliance

As the cybersecurity landscape continues to evolve, so do the compliance requirements imposed by regulators. In many sectors, continuous penetration testing is becoming the standard for demonstrating robust security practices.

Increased Regulatory Scrutiny

Regulatory bodies worldwide are recognising the limitations of periodic penetration testing and pushing for continuous testing to ensure ongoing security. The shift towards continuous penetration testing aligns with the broader trend of continuous compliance, where organisations must demonstrate they meet security and regulatory requirements consistently – not just during periodic assessments.

For example, DORA, which applies to financial institutions across the EU, emphasises operational resilience. DORA will require continuous testing and monitoring of systems to ensure resilience against cyber threats and operational disruptions.

Similarly, the NIST cybersecurity framework in the US encourages organisations to continuously assess and improve their security posture. While continuous testing is not yet mandated across all sectors, it is rapidly becoming a best practice for organisations looking to stay ahead of regulatory requirements and avoid costly fines.

Impact on Cloud Service Providers

Cloud service providers offering PaaS, SaaS and Infrastructure-as-a-Service (IaaS) solutions are under increasing pressure to demonstrate their commitment to security. Many organisations now require service providers to undergo continuous penetration testing as part of contractual agreements, particularly in highly regulated industries such as finance, healthcare and government.

As organisations increasingly move to the cloud, securing these environments is critical. Continuous penetration testing allows cloud service providers to demonstrate that they are continuously monitoring and securing their infrastructure and applications. This not only builds trust with customers but also ensures compliance with industry standards and regulations.

Supply Chain Security

The rise in supply chain attacks, where threat actors target third party vendors or service providers, has made supply chain security a growing concern. Continuous penetration testing is becoming an essential component of supply chain security, helping organisations identify vulnerabilities in the systems of their service providers. Requiring service providers to undergo continuous testing ensures the entire supply chain remains secure.

The Importance of Continuous Penetration Testing for Service Providers

As organisations increasingly rely on third party services for critical operations, ensuring the security of service providers has become a top priority. Providers offering PaaS, SaaS and other technical solutions must demonstrate their commitment to security by undergoing continuous penetration testing.

Building Trust with Clients

Continuous penetration testing allows service providers to build trust with clients by demonstrating they are continuously monitoring and securing their systems. This is especially important in industries such as finance and healthcare, where data security is paramount. Clients want assurance that service providers are taking every possible step to protect their data and maintain service integrity.

Demonstrating Compliance with Industry Standards

Service providers must comply with industry standards and regulations to remain competitive. Continuous penetration testing helps providers meet the security requirements of clients and regulators. This is crucial for providers serving clients in highly regulated industries, where failing to meet security standards can result in significant penalties and reputational damage.

Proactively Identifying and Addressing Vulnerabilities

Service providers face the same cybersecurity challenges as their clients, including the need to identify and remediate vulnerabilities in real time. Continuous penetration testing allows providers to stay ahead of cyber threats by proactively identifying and addressing vulnerabilities before they can be exploited.

10 Tips for Choosing a Continuous Penetration Testing Provider

When selecting a continuous penetration testing provider, organisations should consider several factors:

1. Ensure that operators and penetration testers are directly employed by the organisation, not crowdsourced.
2. Verify that the provider is not offering Penetration Testing as a Service (PTaaS), as this differs from continuous penetration testing.
3. Confirm that the provider has extensive expertise in continuous penetration testing.
4. Ensure the provider offers regular updates on identified vulnerabilities and how to address them.
5. Check if the provider offers monitoring services for continuous protection.
6. Evaluate the provider’s reputation through reviews and feedback from previous clients.
7. Ensure the provider adheres to industry standards and regulations for ethical hacking.
8. Ensure you will be supplied with comprehensive reports detailing vulnerabilities, risks and recommendations.
9. Seek a provider that offers both automated scanning and manual testing for thorough coverage.
10. Weigh the cost versus value. While pricing is important, it’s essential not to compromise on quality in pursuit of savings.

If you’re interested in exploring continuous penetration testing further, Razorthorn Security is here to help. We’ve developed Razor’s Edge, an advanced continuous penetration testing solution designed to provide real time assessments of your infrastructure, applications and systems combining both automation and manual verification and expert analysis.

Razor’s Edge helps you stay ahead of emerging threats and addresses vulnerabilities before they can be exploited. Razor’s Edge delivers comprehensive coverage and actionable insights tailored to your security needs.

Get in touch to discover how Razor’s Edge can protect your organisation against evolving cyber threats.