Feeling confident that your security posture remains consistent between security tests or periodic penetration testing can be a significant challenge for security leaders, especially in organisations that frequently release new features or regularly set up new accounts.

Continuous security assurance provides peace of mind, transforming your strategy from ‘point in time snapshots’ of your posture to an ongoing understanding of relevant security vulnerabilities and evolving threats.

Pentesting is one part of a broader, measurable, auditable assurance loop. Businesses can tackle several crucial components of cybersecurity at once. Compliance requirements and audit-related controls are no longer reactivebut embedded into your security strategy. Remedial action becomes faster, and security becomes tighter.

Let’s explore how continuous assurance can strengthen your enterprise’s existing security function.

What is continuous assurance?

• Continuous assurance is an ongoing security process that provides real-time visibility into your organisation’s security posture.
• It moves beyond traditional point-in-time assessments by continuously monitoring and testing your systems to identify vulnerabilities, manage risks, and ensure compliance.
• It reduces the window of exposure between tests, turning compliance into a continuous stream of evidence for auditors and building greater trust with the board and customers.

The pillars of continuous assurance

The best way to understand continuous assurance is to view it as four interconnected pillars that work together to identify potential threats, support risk management, and provide your security teams with insights into the effectiveness of internal controls.

Continuous asset discovery and inventory

Continuous asset discovery and inventory means knowing the ins and outs of your attack surface so you can effectively secure it. This involves automatically discovering new cloud accounts, subdomains, containers, APIs, endpoints, and more as they are created.

Regular pentests should include a sample of these newly discovered assets, rather than testing the same static scope every time, to ensure comprehensive coverage.

Why it matters:

• Closes blind spots from shadow IT and drift, ensuring new assets are automatically included in scanning and pentesting scope.

Always-on vulnerability and configuration scanning

Always-on vulnerability scanning is an automated process that runs continuously, feeding findings into your pentest programme. This includes automated SAST, DAST, SCA, container, and infrastructure scanning at every stage of the pipeline and in production.

Why it matters:

• Catches low-hanging issues early and fast (shift-left). Provides a baseline of risk that pentesters can validate and exploit.
• Scanner results are used as a starting point: pentests can chain findings, business logic flaws, and exploitability that vulnerability scanning alone might miss.

Regular, scheduled penetration testing

Regular, scheduled penetration testing work is performed by periodically simulating real-world attacks on apps, APIs, cloud, and internal networks. Penetration testing helps evaluate control effectiveness within your existing security strategy and reveal vulnerabilities that vulnerability scanning alone might miss.

Pentests should be scheduled as part of the assurance cycle, with the findings feeding back into the scanning and remediation process.

Why it matters:

• Pentesting validates that vulnerabilities are exploitable and provides accurate insight into what the real impact would be for your business.
• Provides evidence for compliance that controls are working.
• Provides human-led, high-fidelity validation alongside more automated security measures.
• A key component of most popular compliance programs.

Centralised governance and evidence

Centralised governance refers to a central platform or process that aggregates findings from all your continuous monitoring, vulnerability scans, pentests, and other security controls. It then uses this information to generate evidence of your current security posture.

Pentest reports are integrated into the same workflow, so vulnerabilities are tracked alongside scanner findings and remediation SLAs. Learn more about how to actually evaluate a pentest report– explained by cybersecurity experts.

Why it matters:

• Eliminates lots of spreadsheets and fragmented data
• It provides a clear view of risk over time, making audit prep and compliance activities predictable: dashboards and reports can be exported on demand.
• Huge help in meeting major regulatory compliance requirements, such as ISO-27001, SOC 2 Type 2, and PCI-DSS.
• Helps determine next steps in a concise and actionable way, bringing together a broad spectrum of data for an overview of your entire security environment.

How to build your continuous assurance programme

Now you know just how beneficial continuous assurance can be to securing your business, you may be wondering how to actionably implement it. It’s always wise to start small with any continuous assurance introductions into an existing security strategy, then scale the approach appropriately to your business case and budget.

Define scope and cadence

• Consider what you want your security testing to cover and how often to test it, based on your enterprise’s and industry’s risk and compliance needs
• Identify critical assets, set a baseline cadence (i.e., continuous scanning, quarterly pentests)
• Consider how quickly you deploy changes in your CI/CD pipeline: faster deployment cycles generally require more frequent risk management methods.
• Align this with relevant regulatory compliance to justify frequency and scope to your board.

Integrate pentesting into the assurance loop

• Wean away from one-off or fragmented, infrequent pentests to a more continuous pentesting structure.
• Schedule them in advance, use the same scope and template each time (with room to add new assets).
• Be sure to feed pentest findings into the same system as scanner findings, and look for a platform like OnSecurity that provides real-time reporting and free retesting to close the loop quickly.

Establish clear ownership and SLAs

• Define clear roles to avoid security teams owning everything
• Assign issue owners (e.g., product teams, cloud teams) responsible for their scope
• The security team owns the programme, metrics, and escalation
• Set SLAs for issue resolution to ensure accountability
• Use automation to enforce SLAs and track progress efficiently

Monitor and track progress

• Give concrete metrics and KPIs that leaders can use to show progress and justify investment, helping you to attain further funding from your board and emphasise the impact of continuous security. Some strong statistics to mention include:
  • MTTD and MTTR
  • % of critical findings remediated within SLA
  • Trend in critical/high vulnerabilities over time
  • % of systems with exploitable vulnerabilities
• Establish a clear reporting cadence, for example a weekly security team dashboard or a monthly leadership/board report, to show the ongoing effectiveness of your security efforts.

How to Keep Your Continuous Security Testing Programme Running and Improving

Maintaining a continuous assurance programme requires commitment and practical strategies to ensure it remains effective and sustainable over time. Here are key tips to keep your programme going strong:

Automate as much as possible: Use automation to automatically discover new assets for inclusion in scanners and penetration tests, and automatically create and assign remediation tickets. This reduces manual workload and helps keep your attack surface coverage up to date.

Review and refine regularly: Continuously monitor metrics and trends to assess programme performance. Adjust testing frequency, scope, and priorities based on evolving risks and stakeholder feedback to maintain focus on what matters most.

Build a culture of shared responsibility: Train developers, product owners, and other teams on interpreting findings and implementing fixes. Celebrate remediation successes to encourage engagement and reinforce the importance of security across the organisation.

Make continuous assurance practical and scalable with OnSecurity

Ongoing assurance doesn’t have to feel like an intimidating security endeavour. OnSecurity’s platform-based pentesting services integrate seamlessly into your assurance loop, optimising manual processes and providing a continuous source of risk reduction without the stress of endless overheads.

Find out more about OnSecurity’s penetration testing services today.