“DLP Failures: When Data Loss Prevention Doesn’t Prevent Anything”

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DLP Can’t Detect Encrypted Exfiltration

Files sent over HTTPS, VPN, or encrypted zip bypass inspection. Even when flagged, DLP can’t decrypt or analyze payloads. Sensitive data flows out silently under a secure wrapper.

Regex Rules Miss Contextual Leaks

DLP relies on patterns — like SSNs or keywords — not intent. Clever attackers reformat or encode data to avoid triggers. Important leaks happen through unstructured, indirect content.

False Positives Desensitize Security Teams

Constant alerts about false leaks reduce response quality. Teams ignore or auto-dismiss DLP warnings. Real data loss is buried under noise and fatigue.

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Insider Threats Know How to Work Around DLP

Employees with access know what triggers alerts — and what doesn’t. They use private email, screenshots, or cloud sync tools. DLP can’t stop what it can’t see.

Endpoint DLP Agents Are Disabled or Misconfigured

DLP tools on laptops may not survive OS updates or admin tampering. No agent means no monitoring. Endpoint coverage is assumed — not confirmed.

DLP in SaaS Apps Lags Behind Shadow Usage

Files shared in Google Docs or pasted into Slack escape detection. Most SaaS DLP integrations are shallow or missing entirely. Data walks out through tools security doesn’t monitor.

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