How ShadowSight Applies the OODA Loop to Insider Risk and Data Leakage Prevention

ShadowSight is built from the ground up to handle data leakage and insider threats—unauthorised actions taken by authorised users. Using the OODA Loop framework (Observe, Orient, Decide, Act), ShadowSight drives faster, smarter, and more accurate threat detection by focusing on what matters: high-risk behaviour in context.

Observe: Focused, Non-Disruptive Monitoring

ShadowSight tracks activity across endpoints, communication platforms, file movements, and cloud storage, without disrupting workflows. It collects telemetry in near real time—capturing what users do, not just anomalies. This includes authorised but risky actions like uploading sensitive data to personal cloud storage or emailing confidential files to private accounts.

Unlike traditional systems that overwhelm with alerts, ShadowSight filters noise. It ignores low-risk and routine behaviour so analysts can focus on real threats.

Orient: Context That Actually Means Something

Data without context is just noise. ShadowSight uses what we call “collective intelligence” —combining role, past activity, behavioural baselines, data classification and organisational norms to determine what’s actually risky. It integrates insights from HR, Legal, and Team Leaders to provide richer insights.

This “collective intelligence” reduces false positives and increases accuracy by asking the right question: Is this risky for this person, in this role, at this time?

Decide: Human-Led Responses, Backed by Context

ShadowSight supports decision-making by giving analysts and business stakeholders clear, contextual insight into user activity. Rather than relying solely on automation, it enables informed, risk-based judgment through a combination of behavioural baselines, role-based context, and data sensitivity. Teams can quickly create or adjust rules without needing technical skills, allowing HR, Legal, and Security to shape responses to fit real-world scenarios. This flexibility ensures that decisions—whether to escalate, investigate, or monitor—are aligned with organisational priorities and not just system defaults.

ShadowSight puts control in the hands of people, not just algorithms.

Act: Proportionate, Targeted Response

When a threat is real, ShadowSight acts immediately. It might trigger an alert, highlight potential access risks or suggest further investigation, with full support for compliance and audit requirements. ShadowSight’s role is to guide proportionate responses that prevent data leakage while allowing legitimate work to continue uninterrupted.

This is where ShadowSight stands apart: it doesn’t default to blocking. It empowers organisations to respond with precision, preserving business continuity while addressing the risk.

Close the Loop: Learn, Adapt, Improve

ShadowSight supports continuous improvement by capturing insights from each incident. As teams review and respond to alerts, they can refine rules, adjust thresholds, and improve context—making the platform more effective at highlighting genuine risks and reducing noise over time.

Why It Works

Most data leakage happens through authorised activity—things users are allowed to do, but shouldn’t. ShadowSight understands this and was purpose-built to handle it. The OODA Loop isn’t just a conceptual model—it’s embedded in how ShadowSight works, making detection faster, decisions sharper, and interventions smarter.

This loop—observe, orient, decide, act—happens continuously, powered by ShadowSight’s near real-time telemetry, collective intelligence, and risk-based prioritisation. The result: fewer false positives, faster responses, and better protection of your most critical assets.

Christopher McNaughton

Strategic Advisor, ShadowSight

Who is Christopher McNaughton

With over three decades of experience in law enforcement, corporate investigations, and digital forensics, Christopher McNaughton has led complex investigations across both public and private sectors. As a Detective with Victoria Police, he specialised in organised crime and serious sex crime investigations, before transitioning to General Electric 2007. At GE, he served as Senior Director of Global Forensics, Investigations, and Insider Threat, managing forensic analysis, eDiscovery, and risk mitigation across multinational operations.

Now the Managing Director of SECMON1 and ShadowSight, Christopher helps organisations tackle fraud, corruption, insider threats, and cyber risks through advanced forensic techniques. A Certified Digital Forensic Examiner with NV1 security clearance, he is a trusted expert in litigation support, data governance, and digital investigations, ensuring businesses stay ahead of evolving threats.

What is ShadowSight

ShadowSight is a data leakage prevention and insider risk management platform. It combines behavior analytics, SEIM and an integrated workflow to dynamically adjust to business risk. Staff activity is risk rated and reviewed to highlight risky events.