I want to talk about the Microsoft 365 Copilot bug. Not because it was exceptional, but because what it exposed should change how every organization architects AI governance. For weeks at the beginning of the year, Microsoft 365 Copilot read and summarized confidential emails despite sensitivity labels and Data Loss Prevention policies being correctly configured to block that behavior. The bug, tracked as CW1226324, affected emails in users’ Sent Items and Drafts folders. Legal communications. Business agreements. Protected health information. All processed by an AI that explicitly stated organizational policies said should never touch it. Microsoft’s response was that users…
Tim Freestone
Tim Freestone
Tim Freestone, the chief strategy officer at Kiteworks, is a senior leader with more than 17 years of expertise in marketing leadership, brand strategy, and process and organizational optimization. Since joining Kiteworks in 2021, he has played a pivotal role in shaping the global landscape of content governance, compliance, and protection.