How Continuous Penetration Testing Can Help You Achieve Proactive Protection

The Canadian Cybersecurity Study shows that cyberattacks in Canada are becoming more effective at breaching defences, with the attack-to-incident success rate increasing compared to previous years. This trend signals that recent threats are not only more sophisticated but also harder to stop.

As per the study, Canadian organizations reported 20–25 security incidents annually on average across a range of categories, including denial of service (DoS) attacks, infiltration attempts, data breaches and cloud-related compromises.

Such persistent and varied threats highlight the need for a security strategy that keeps pace with attackers’ evolving tactics.

In this threat landscape, continuous validation of security controls is no longer optional – it’s a necessity. By testing defences regularly against emerging attack methods, organizations can shift from a reactive posture to a proactive, resilient security strategy that anticipates and mitigates risks before they cause damage.

The benefits of continuous penetration testing

Modern penetration testing programs help bridge the gaps and risks associated with one-off or infrequent security tests, significantly improving an organization’s overall resilience.

According to the Canadian Cybersecurity Study, 81 percent of respondents reported that penetration testing had uncovered issues that could have prevented major breaches. This underscores the value of moving from periodic testing to a continuous model.

Unlike traditional point-in-time assessments, continuous penetration testing delivers ongoing visibility into the security posture. It also ensures that new vulnerabilities are identified and addressed promptly.

Key benefits include the following:

• Heightened cybersecurity preparedness: Regular, iterative security assessments such as penetration testing, vulnerability scans and configuration reviews enable organizations to detect weaknesses before they are exploited. This proactive approach helps refine defences, validate incident response capabilities and maintain readiness against evolving cyberthreats.
• Identify and address vulnerabilities quickly: Early detection of misconfigurations, outdated software or insecure practices allows security teams to patch and remediate before attackers can exploit them. This reduces the “window of exposure” and strengthens the organization’s overall security framework.
• Ensure ongoing resilience: As attack vectors, threat actors and technologies evolve, continuous testing helps organizations adapt in real time. By combining consistent validation with threat intelligence, businesses can maintain an agile security posture capable of withstanding emerging risks.
• Support compliance and audit readiness: Many regulatory and industry standards such as ISO 27001, SOC 2 and NIST require regular or ongoing security testing. Continuous penetration testing ensures that evidence of security due diligence is readily available, streamlining audit processes and reducing last-minute compliance pressure.

Continuous penetration testing is not just a defensive tactic – it’s a strategic investment that embeds security into daily operations, reduces breach likelihood and builds long-term trust with customers, partners and regulators.

The following three ways can help organizations modernize their penetration testing strategy to better protect their environments and reduce breach risks.

Traditional penetration tests provide valuable insight, but their static nature means vulnerabilities can go undetected between assessments. Continuous pen testing offers greater insight into the security preparedness of an IT environment with periodic tests that highlight potential vulnerabilities.

The process involves a layered framework combining automated vulnerability scanning, penetration testing and configuration reviews. This allows security teams to detect misconfigurations, outdated components and exploitable weaknesses in real time before attackers do.

Building a continuous penetration testing process can be complex due to the resources, coordination and tools required. However, organizations can break it down into structured, manageable steps to gradually mature their security operations.

The following strategies can help organizations transition to a continuous penetration testing approach.

Assess your current security maturity

According to the Canadian Cybersecurity Study, only 4.2 percent of organizations with a basic level of security maturity conduct continuous penetration testing. This means the vast majority may still be relying on periodic or ad-hoc testing, leaving potential blind spots between assessments.

Begin by reviewing your current security posture, including how often testing occurs, the scope of your assessments and the depth of remediation follow-up.

Consider questions such as:

• Are we identifying vulnerabilities in real time or only during scheduled intervals?
• How quickly are findings communicated to stakeholders?
• Are we testing all of our attack surfaces?

From there, develop a roadmap for improvement. Define specific objectives for continuous penetration testing such as improving detection speed, validating security controls against evolving threats or reducing breach risk exposure and tie them to measurable KPIs. This clarity will help ensure your transition aligns with broader business and risk management goals.

Choose a testing framework

A well-chosen testing framework provides structure by establishing requirements, tools, reporting methods and escalation procedures. The right framework should reflect your security environment’s architecture and address identified gaps.

For example: If your environment is heavily cloud-based, look for a framework that supports cloud-native testing methodologies and integrates with cloud security monitoring tools.

Alternatively, if you have a hybrid environment, ensure the framework covers both on-premises infrastructure and cloud workloads without leaving weak spots.

Here are three widely recognized options:

• MITRE ATT&CK: Maps adversary tactics, techniques and procedures (TTPs) to real-world threat scenarios, enabling teams to test defences against the most relevant and likely attacks.
• OWASP testing guide: Focuses on application security, providing a detailed methodology for identifying vulnerabilities such as injection flaws, authentication weaknesses and insecure configurations.
• NIST SP 800-115: Offers a structured approach to planning, executing and reporting on penetration tests. It covers network, application and physical security.

By leveraging these or similar frameworks, organizations can ensure testing is comprehensive, methodical and aligned with industry best practices.

Beyond the framework itself, encourage collaboration between cybersecurity teams, IT operations and application development teams. This ensures that remediation is prompt and integrated into the organization’s security culture.

Integrate with DevOps pipelines

For organizations with internal software development, embedding penetration testing directly into the DevSecOps lifecycle is crucial. This means security checks happen before code is deployed, rather than being bolted on afterward.

Key integration steps include:

• Automating vulnerability scans during build and deployment phases.
• Using static and dynamic application security testing (SAST/DAST) tools in the pipeline.
• Creating feedback loops so developers receive actionable, prioritized findings quickly.
• Ensuring that critical vulnerabilities block releases until they are remediated.

When continuous testing is part of the DevOps pipeline, security shifts left and moves closer to the start of the development process. This results in faster remediation, reduced costs and fewer vulnerabilities making it to production.

Chris Graziano, Managing Consultant – Offensive Security Team, CDW Canada, points out, “You should always be testing your applications before they’re published, including when updates are made. Regular security testing should be integral as part of development process.”

Canadian organizations have generally maintained strong security practices for on-premises infrastructure, but testing in hybrid environments often lags behind. The Canadian Cybersecurity Study found that only 45.6 percent of respondents use cloud-specific security testing tools, leaving potential blind spots in hybrid environments that combine on-premises and cloud services.

As digital estates grow more complex, these gaps become more dangerous. The introduction of AI systems and the reliance on third-party providers have expanded the attack surface, making it critical for organizations to broaden the scope of their security testing.

Graziano emphasizes: “Ensure you're testing all your organization's environments, whether that is your network, your applications, your cloud or your LLMs.
Make sure special attention is paid to any of these environments in which a third-party has access.” 

Types of environments that security testing should cover

• Cloud environments: Infrastructure, platforms and services hosted on providers like AWS, Azure or Google Cloud, where misconfigurations or weak access controls can be exploited.
• Network infrastructure: Physical and virtual components such as servers, routers, switches and firewalls that form the backbone of business operations.
• Applications: Web, mobile and desktop software, including APIs, which are common targets for data theft and service disruption.
• LLM and AI systems: Machine learning models and generative AI platforms that may be vulnerable to adversarial inputs, model poisoning or data leakage.
• Third-party ecosystems: External vendors, SaaS providers, contractors and partners that integrate with your systems, potentially introducing new vulnerabilities.

Partnering with experienced security professionals can help organizations address common challenges such as skill gaps, the absence of an internal SOC and difficulties in selecting the right testing framework.

Smaller organizations, in particular, often struggle to design penetration testing processes that deliver meaningful results. By engaging external specialists, they can reduce the time and cost of building an effective, well-structured testing program.

“From a testing perspective, having the right experts, tools and the experience to know when certain activities should or shouldn’t be part of a penetration test is crucial,” says Graziano.


Many Canadian organizations are already turning to managed detection and response (MDR) providers for this type of expertise. The Canadian Cybersecurity Study found that 41.1 percent of respondents have partnered with an MDR provider, with 73.2 percent citing “improving the ability to prevent or mitigate security breaches” as their top reason. The same benefits (specialized skills, proven tools and efficient methodologies) apply when building a penetration testing program.

Security experts can help organizations in the following ways:

Provide access to advanced skills and tools

Experts can offer guidance on leveraging advanced skills with a lower learning curve for organizations. They can help implement, train and operate security testing programs that equip organizations with improved defences against sophisticated threats.

Conduct threat emulation exercises

Threat emulation exercises can help security teams align with real-world adversary behaviour. They can validate whether security controls would actually detect or stop an attack. Security experts can facilitate a red team or purple team exercise to guide security testing improvements.

Conduct tailored assessments for complex environments

Expert-led risk assessments go a long way in surfacing complex threats and developing remediation plans. With experience in identifying risks across third-party integrations, shadow IT and supply chain, experts can draft strategies for cyberincident prevention with greater accuracy.

As organizations seek to evolve their security testing processes, they may find the threat landscape difficult to navigate. CDW Canada’s risk advisory experts offer key services to help raise testing and threat identification capabilities.

“We have the breadth and the depth to assist customers anywhere in their cybersecurity journey. We meet them where they are, whether it's MDR services, penetration testing services, implementing technologies, security controls or managing their security operations.
We have the capability, maturity, the expertise and the depth to assist them in their journey,” said Ben Boi-Doku, Chief Strategist, Cybersecurity Services Strategy & Development, CDW Canada.

From risk assessment to program implementation, CDW experts collaborate with your security team to deliver on security expectations. With an all-Canadian security team and security operations centre (SOC), we enable you to reduce security risks based on your unique IT environment.