Explore privacy vulnerabilities in observability platforms through an offensive security research lens in this 17-minute conference talk from PEPR '25. Examine how observability systems that collect logs, metrics, traces, and telemetry data for distributed system monitoring can inadvertently expose sensitive user information despite aggregation techniques. Learn about reconstruction attacks conducted against aggregated user session data and discover how offensive privacy research methodologies can strengthen business cases for implementing new privacy protection features. Understand the unique challenges of privacy threat modeling in business-to-business environments and investigate runtime mitigation strategies designed to interrupt reconstruction attacks early in the privacy kill chain, helping organizations balance operational visibility with user privacy protection.