Don't Bet the Business

Earlier this year, a federal court determined that a defendant’s communications with a Large Language Model (LLM or AI) – specifically, Claude – regarding pending criminal charges against him were discoverable and unprotected by attorney-client privilege. United States v. Heppner, 820 F. Supp. 3d 292, 297 (S.D.N.Y. 2026).

This ruling is in keeping with longstanding attorney-client privilege interpretations; chiefly, that only communications between counsel and the client can be subject to the attorney-client privilege. The U.S. District Court for the Southern District of New York (SDNY) held that: “AI Documents are not like confidential notes that a client prepares with the intent of sharing them with an attorney because Heppner first shared the equivalent of his notes with a third party, Claude.”

Much has been written about the increasing reliance on AI chatbots, AI personal assistants, and AI even serving as a companion. The risk here is that clients believe their AI tools are an essential part of their work and, therefore, also believe their interactions with the LLM are privileged. But a client’s communications with open-source LLMs are likely not privileged. In a different federal ruling, the SDNY held that “[i]n the absence of an attorney-client relationship, the discussion of legal issues between two non-attorneys is not protected by attorney-client privilege.”

Increasingly, litigating attorneys are explicitly asking for the opposing party’s prompts submitted to AI. These prompts can reveal a client’s mental impressions, as well as their attorney’s. While there is no Illinois state court case that directly mirrors the SDNY’s analysis in Heppner, it stands to reason that its analysis will be adopted.

Illinois courts have a strong public policy in favor of disclosure. The Illinois Supreme Court held in Waste Mgmt., Inc. v. Int'l Surplus Lines Ins. Co. “that in Illinois, we adhere to a strong policy of encouraging disclosure, with an eye toward ascertaining that truth which is essential to the proper disposition of a lawsuit.” It remains the policy of Illinois courts to allow for discovery on any relevant matter and that “the [attorney-client] privilege ought to be strictly confined within its narrowest possible limits.” Id. (emphasis added).

In sum, people who are in active litigation, are considering litigation, or have ongoing concerns about discovery disclosures should be wary of asking any LLM for legal advice. An AI prompt is almost certainly discoverable in litigation. In order for litigants to protect themselves against unintentionally waiving privilege, legal questions should be directed to counsel and only to counsel.