Episode summary. On February 17, 2026, federal Judge Jed Rakoff issued the first nationwide ruling holding that conversations with consumer AI chatbots are not protected by attorney-client privilege and are fully discoverable in litigation. Six weeks later, the Delaware Court of Chancery used a CEO's deleted AI chat logs as trial evidence in a $250 million earnout dispute. This episode walks CEOs, GCs, and CISOs through what the courts actually held, what it means for your company in practice, and the five specific moves to make this week.

Why this matters. Every prompt your employees type into ChatGPT, Claude, Gemini, or Copilot is now a timestamped, logged document living on a third party's servers under terms that explicitly permit disclosure to regulators and courts. The candor of AI conversations — pre ...