In this webinar hosted by TechStrong, Michael Roberts, Security Engineer at Cresta, and Or Guz, VP of Customer Success at Bold Security, sit down for a practitioner deep dive on endpoint data loss prevention in the age of AI. They cover why static data classification and tagging break down at scale, how to attribute activity when no person is at the keyboard, what everyday enforcement gets wrong, and why blunt blocking eventually pushes teams to weaken or disable it. The takeaway: context about the data, the user, and the destination is what separates real risk from routine work, and it’s what lets you stop data loss without stopping the business.