Two U.S. federal court decisions – both issued in February 2026 – reached opposite conclusions on whether interactions with generative AI platforms are protected by attorney‑client privilege or the work‑product doctrine. In the Southern District of New York, in United States v. Heppner, Judge Jed Rakoff ruled that a criminal defendant’s exchanges with Claude were not protected. Yet, in the Eastern District of Michigan, in Warner v. Gilbarco, Inc., Magistrate Judge Anthony Patti held that documents and information related to a pro se plaintiff’s use of ChatGPT were shielded from discovery. With insights from BakerHostetler, Hunton Andrews Kurth and Morrison Foerster partners, this article parsed the courts’ analyses, examined the implications of this developing body of case law and offered practical takeaways regarding protections of AI inputs and outputs.