Data Loss Prevention (DLP) is one of the most widely implemented and most widely distrusted controls in Microsoft 365. Policies generate noise, users ignore warnings, and security teams quietly reduce enforcement just to keep the business running.

In this session, we take an honest look at why DLP fails in real-world environments and what it takes to make it effective. Using Microsoft Purview, we’ll walk through the gap between how DLP is designed and how it actually behaves in day-to-day collaboration across SharePoint, Teams, and Exchange.

Rather than focusing on theory, this session is built around two live demos that support a clear narrative:

First, we’ll demonstrate a typical “broken” DLP implementation. You’ll see how overly broad policies, lack of context, and generic policy tips create false positives and user confusion-ultimately leading to risky workarounds and loss of trust in the system.

Next, we’ll rebuild the same scenario using a practical, experience-driven approach. By introducing classification, reducing scope, and improving user-centric policy design, you’ll see how DLP can shift from noisy enforcement to meaningful risk reduction.

Along the way, we’ll connect these examples to common implementation mistakes and show how to redesign your DLP strategy around real business scenarios instead of compliance checklists.

This is not a feature walkthrough it’s a reality check, backed by practical demonstrations, on how to make DLP work in Microsoft 365 environments where people, data, and collaboration are constantly evolving.

Assumed Knowledge:

Basic DLP concepts and terminology; Microsoft 365 workloads and data flows; Sensitivity labels and classification basics;

Practical Takeaways:

Why traditional DLP approaches fail in M365 environments; How to reduce false positives and improve signal-to-noise ratio; How to design user-friendly DLP policies that people won’t bypass; How to align DLP with real business scenarios instead of theory; A practical framework for improving existing DLP deployments;

Out of Session Scope:

We will not cover initial setup of DLP from scratch, or deep dives into regex or custom pattern development.