Artificial Intelligence chatbots are ubiquitous at this point. Millions of Americans use these tools daily in both their professional and personal lives. They’re great tools for quickly compiling information, gaining insight into discrete questions, and creating first drafts of documents. But, like any tool, there are potential pitfalls associated with their use. The Southern District of New York addressed a novel issue created by a litigant’s AI use in a memorandum published earlier this month: “Whether, when a user communicates with a publicly available AI platform in connection with a pending criminal investigation, are the AI user’s communications protected by attorney-client privilege or the work product doctrine?”[1] The short answer is no.
Attorney-client privilege and the work-product doctrine are cornerstones of the American legal system. Attorney-client privilege protects confidential communications between a client and counsel made for the purpose of obtaining legal advice. The work-product doctrine, by contrast, shields materials prepared by or at the direction of counsel in anticipation of litigation, particularly those reflecting an attorney’s mental impressions, legal theories, and strategy. Courts construe both doctrines narrowly because they operate as exceptions to the general rule favoring broad discovery and full disclosure of relevant evidence.
In United States v. Heppner, a criminal action for securities fraud pending in the Southern District of New York, the defendant independently used a publicly available AI-chatbot to draft analyses of potential legal arguments and defenses after learning he was the target of a federal investigation and receiving a grand jury subpoena. Federal agents later seized those AI-generated materials pursuant to a search warrant. The defendant later asserted that the documents were protected by attorney-client privilege and the work-product doctrine, even though his counsel had not directed or supervised the use of the AI platform.
In a February 17, 2026, memorandum opinion, Judge Jed Rakoff rejected both claims of protection. With respect to attorney-client privilege, the court emphasized that communications with a generative AI platform are not communications with an attorney and therefore fail at the threshold. The court also found that confidentiality was lacking. The platform’s publicly available privacy policy disclosed that user inputs and outputs could be retained, used for training, and shared with third parties, including government authorities. Because the defendant voluntarily disclosed information to a third party without a reasonable expectation of confidentiality, the communications were not privileged when made and did not later become privileged simply because they were shared with counsel.
The court reached a similar conclusion under the work-product doctrine. Although the defendant created the materials after it became clear that litigation was anticipated, the documents were not prepared by or at counsel’s direction. They did not reflect counsel’s strategy at the time they were generated. The court reiterated that the doctrine exists to protect the mental processes of lawyers, not to shield every litigation-related document a client independently creates. Extending work-product protection to such materials, the court explained, would undermine the doctrine’s purpose and expand it beyond its established limits.
While North Carolina courts have not considered the issue, the Heppner decision serves as a practical warning for businesses and individuals in any jurisdiction—be cautious with AI when using it in connection with a legal dispute. Generative AI tools may be useful, but using them in connection with litigation can potentially create discoverable material that would otherwise be protected by attorney-client privilege or the work product doctrine. Before using AI to gain insight into potential legal issues, clients should consult with their attorneys to understand the risks and to ensure that strategic decisions are made within the boundaries of existing privilege law.
[1] United States v. Heppner, No. 25‑cr‑00503 (JSR), Memorandum Opinion (S.D.N.Y. Feb. 17, 2026).
