The Moral Machine host Chris D. Warren interviews Morristown, New Jersey federal criminal defense attorney Ernesto Cerimele about the New York Times v. OpenAI lawsuit and Judge Wang’s May preservation order requiring OpenAI to retain all U.S. user-submitted materials. They argue the order’s scale (billions of users/chats) creates an unprecedented pool of private, potentially confidential AI chat logs, raising Fourth Amendment concerns under Carpenter and limits on the third-party doctrine for modern digital data. Cerimele discusses risks of general warrants, overbroad subpoenas, and law enforcement access to preserved logs revealing politics, health, relationships, and legal strategy. Proposed guardrails include search-warrant requirements, particularity (timeframes/keywords/topics), minimization akin to wiretap rules, filter teams for privilege, and stronger judicial oversight, citing New Jersey’s State v. Benoa suppressing an overbroad four-year phone search.

What really happens to client data when you use tools like ChatGPT, especially if you click “delete” or disable training? In this episode, I’m joined by Cathy Miron, CEO of eSilo and a nationally recognized expert in data protection and cybersecurity, to unpack the privacy, security, and governance realities behind modern LLMs. We discuss litigation and vendor policies can complicate “private” chats, why backups, logs, and engineering choices often outpace contract language, and practical ways lawyers and regulated organizations can use AI without compromising confidentiality or privilege. We cover de-identification workflows, BAAs and vetted tools (think FedRAMP/CMMC contexts), API nuances around ZDR, and the human firewall. Governance for acceptable-use policies, training, and curbing “shadow AI” with sanctioned, enterprise subscriptions. It’s a candid, pragmatic guide to balancing innovation with risk.