Looking for Legal Advice From AI? It Can and May Be Used Against You in a Court of Law

Recently, I discussed the many reasons that trying to use generative AI platforms such as ChatGPT and Claude instead of an attorney for legal advice and guidance is a fool’s errand. From getting the law wrong (and not being able to sue for malpractice) to not knowing the nuances of your particular circumstances, needs, or goals, AI lacks the insights, understanding, and personal relationships that form the core of a strong and productive attorney-client relationship. Now, for the first time, a federal court has found that AI lacks one of the other defining characteristics of that relationship: the attorney-client privilege.

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For anyone using AI to get answers to legal questions, but especially for dental professionals who handle protected health information (PHI) about their patients, this lack of confidentiality means that these searches and prompts, and the responses given by the algorithm, are subject to discovery and disclosure in any litigation where they might be relevant. This could not only be embarrassing, but could also torpedo otherwise strong claims and defenses.

In United States v. Heppner, U.S. District Judge Jed S. Rakoff of the U.S. District Court for the Southern District of New York issued a decision on February 17, 2026, addressing what he described as "a question of first impression nationwide: 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?"

Judge Rakoff answered that question with a broadly applicable "no." Although Heppner arose in the context of a criminal investigation and prosecution (and is not binding on courts outside the S.D. of New York), the court's reasoning appears equally relevant to civil litigants who attempt to "do their own research" or otherwise seek legal information or guidance from a generative AI platform without the direction or involvement of counsel.

In Heppner, the U.S. Department of Justice (DOJ) charged the defendant with securities fraud, wire fraud, and related offenses. Following Heppner's arrest, federal agents seized a substantial collection of electronic and hard-copy records, including approximately 31 documents memorializing his communications with the generative AI platform Claude. Those communications took place after Heppner received a grand jury subpoena and learned that he was the target of a criminal investigation.

As the opinion notes, Heppner's counsel acknowledged that, "without any suggestion from counsel that he do so," Heppner "printed reports from Claude that outlined defense strategy, that outlined what he might argue with respect to the facts and the law that we anticipated that the government might be charging."

Heppner argued that these documents were protected by both the attorney-client privilege and the work product doctrine. He contended that he had entered into Claude information he learned from counsel, created the documents for the purpose of discussing them with counsel to obtain legal advice, and later shared the AI-generated materials with his attorney.

Claude Is Not an Attorney, and Communications With It Are Not Confidential

As Judge Rakoff observed, the attorney-client privilege is not absolute and "Courts construe the attorney-client privilege narrowly." He concluded that Heppner's communications with Claude "lack at least two, if not all three, elements of the attorney-client privilege." Specifically:

• Claude is not an attorney. The communications with Claude "are not communications between Heppner and his counsel. Heppner does not, and indeed could not, maintain that Claude is an attorney." As a result, "No such [attorney-client] relationship exists, or could exist, between an AI user and a platform such as Claude."
• The communications were not confidential. The documents did not qualify as confidential because Anthropic's privacy policies informed users that the company may "disclose personal data to third parties in connection with claims, disputes, or litigation." Accordingly, Heppner could not have had a "reasonable expectation of confidentiality in his communications" with Claude.
• The communications were not made for the purpose of obtaining legal advice. Heppner did not communicate with Claude at the direction of counsel, Claude expressly disclaims providing legal advice, and the communications did not become privileged simply because Heppner later shared them with his attorney.

Communications With AI Were Not Attorney Work Product

The work product doctrine, which is closely related to the attorney-client privilege, protects materials prepared by or at the direction of counsel in anticipation of litigation or trial. Judge Rakoff concluded that Heppner's communications with Claude were neither prepared by nor at the direction of counsel and did not reflect defense counsel's litigation strategy. Accordingly, the work product doctrine did not apply.

The law has long had to adapt to emerging technologies, and artificial intelligence is no exception. Heppner is unlikely to be the last case to test how existing legal doctrines apply to AI. As Judge Rakoff concluded, "AI's novelty does not mean that its use is not subject to longstanding legal principles, such as those governing the attorney-client privilege and the work product doctrine."

The practical takeaway is straightforward: anyone seeking legal answers or guidance from a generative AI platform—an approach that carries significant risks in any event—should assume that every prompt submitted and every response generated can and may be used against you in a court of law. 

At Grogan, Hesse & Uditsky, we focus a substantial part of our practice on providing exceptional legal services for dentists and dental practices, as well as orthodontists, periodontists, endodontists, pediatric dentists, and oral surgeons. We bring unique insights and deep commitment to protecting the interests of dental professionals and their practices and welcome the opportunity to work with you.

Please call ddslawyers.com at (630) 833-5533 or contact us online to arrange for your complimentary initial consultation.

Jordan Uditsky, an accomplished businessman and seasoned attorney, combines his experience as a legal counselor and successful entrepreneur to advise dentists and other business owners in the Chicago area. Jordan grew up in a dental family, with his father, grandfather, and sister each owning their own dental practices, and this blend of legal, business, and personal experience provides Jordan with unique insight into his clients’ needs, concerns, and goals.