David S. Kemp analyzes the first federal court ruling on AI and attorney-client privilege, United States v. Heppner, examining the court’s reasoning across each element of the privilege test and the work product doctrine. Mr. Kemp argues that while the court reached the correct result on two independent and sufficient grounds, its unnecessary confidentiality analysis was methodologically flawed—treating Anthropic’s broadest contractual reserved rights as dispositive without examining the specific terms, product tier, or training preferences that actually governed Heppner’s use. He warns that this overbroad reasoning, rather than the uncontroversial holdings, is what future courts will most likely cite, with potentially damaging consequences for privilege claims in any professional context involving third-party platforms.