As the use of artificial intelligence (AI) becomes more prevalent in day-to-day life and in the legal field, in particular, thorny questions arise regarding the implications of that use. One such question is whether exchanges with a publicly available generative AI platform in connection with pending litigation are protected by the attorney-client privilege or the work product doctrine. In a matter of first impression nationwide, U.S. District Judge Jed S. Rakoff of the Southern District of New York answered that question in the negative and required a defendant to provide the prosecution documents memorializing litigation-related communications with a generative AI platform.[1] Applying traditional principles governing the attorney-client privilege and the work product doctrine, the court reasoned that the communications did not involve an attorney-client relationship, were not confidential, were not made for the purpose of obtaining legal advice, and did not reflect an attorney’s trial strategy.[2] The ruling will likely impact whether legal protections are afforded to AI communications, prompts, and output in both litigation and regulatory inquiries, including state attorneys general (AG) investigations.

Background

On October 28, 2025, a grand jury indicted Bradley Heppner on a number of securities and wire fraud charges arising out of misconduct in his role as an executive of several corporations.[3] In the months leading up to the indictment, Heppner became aware that he was the target of the government’s investigation and, anticipating an indictment, began preparing his defense, including by retaining counsel. Heppner also utilized the generative AI platform Claude to prepare reports outlining his defense strategy and his potential arguments moving forward.[4] Importantly, Heppner did so of his own volition and “[w]ithout any suggestion from counsel.”[5] Heppner then provided those documents to his counsel.

On November 4, 2025, the FBI executed a search warrant at Heppner’s home in connection with his arrest.[6] Among the materials seized were 31 documents that memorialized the communications between Heppner and Claude. Heppner contended that those documents were privileged because the communications involved information Heppner learned from counsel and he had created them for the purpose of speaking with his counsel, to whom he ultimately provided the documents.[7]

The government thereafter moved to admit the documents as part of its case-in-chief asserting that the documents were not protected by either the attorney-client privilege or the work product doctrine.[8] The court heard oral argument on that motion on February 10, 2026, and orally granted the motion.[9] On February 17, 2026, the court issued a written memorandum explaining its order.[10]

Judge Rakoff’s Decision

In its written memorandum, the court held that Heppner’s documents failed to satisfy the well-accepted elements of the attorney-client privilege and the work product doctrine.

Attorney-Client Privilege

As to attorney-client privilege, the court concluded that the communications with Claude failed to satisfy any of the privilege’s three elements.[11]

First, the court determined that the communications did not involve an “attorney-client relationship” because neither Heppner nor Claude was an attorney.[12] And the absence of a “trusting human relationship” with a “licensed professional who owes fiduciary duties and is subject to discipline” alone negated the application of the attorney-client privilege.[13]

Second, the court concluded that the communications were “not confidential,” as is required to assert the attorney-client privilege.[14] Beyond the fact that Heppner communicated with a third-party AI platform, Claude’s user consent policy expressly states that it collects data on communications with Claude and that it reserves the right to disclose that data to third parties, including governmental authorities in connection with litigation.[15] Heppner therefore could not have had a “reasonable expectation of confidentiality in his communications.”[16]

Third, although a “closer call,” the court held that Heppner “did not communicate with Claude for the purpose of obtaining legal advice.”[17] While Heppner allegedly communicated with Claude for the “express purpose of talking to counsel,” he did not do so at the “suggestion or direction of counsel.”[18] The court posited that had counsel directed Heppner to utilize Claude, there may have been an argument that Claude acted as counsel’s agent within the protection of the attorney-client privilege. But because the communications were of Heppner’s “own volition,” the only question was whether Heppner intended to obtain legal advice from Claude. And, because he did not, the privilege did not apply.[19] Nonprivileged communications, the court reasoned, cannot be turned into privileged ones simply because they are shared with counsel.[20]

Work Product Doctrine

The court next held that the documents memorializing the communications between Heppner and Claude did not satisfy the elements necessary to invoke the work product doctrine, which protects “materials prepared by or at the behest of counsel in anticipation of litigation or for trial.”[21]

The court explained that, even if the documents were created in anticipation of litigation, they were “not prepared by or at the behest of counsel” and they did not reflect counsel’s trial strategy at the time they were created — though they affected counsel’s strategy moving forward.[22]

Key Takeaways

• The court’s decision is narrow. The court did not conclusively determine that the use of a third-party generative AI tool will always result in mandated disclosure of communications. Rather, the court’s decision is fact-specific, concluding only that the use of AI by a nonattorney that is not undertaken at the behest of an attorney is not covered by the attorney-client privilege or the work product doctrine. The question remains whether the work product doctrine can be invoked if an attorney — or a client at the behest of an attorney — utilizes AI to memorialize the attorney’s thought process in anticipation of litigation. Additionally, the court’s decision is only binding in the Southern District of New York’s federal courts. However, the order could serve as persuasive authority in other jurisdictions given it is a ruling of first impression.
• The ruling will have a regulatory impact. State AGs are increasingly active in the AI space, particularly given the Trump administration’s hands-off approach to AI governance. Indeed, AGs will often seek AI-generated data as part of civil investigative demands and other subpoenas. Given this, AGs are sure to cite the instant decision to pierce claims of privilege and work product as they seek AI communications and data through various processes. It is therefore incumbent upon counsel and businesses to use all due caution when interacting with AI platforms, and certainly if a matter may be subject to future regulatory inquiry.
• The appropriate use of AI in litigation is evolving. Throughout the memorandum, Judge Rakoff noted the novelty of the question presented and highlighted various questions that his opinion did not resolve, such as whether the outcome would have been different if Heppner’s counsel had directed Heppner to utilize Claude. Courts are likely to grapple with these questions in the immediate future. Counsel and businesses should thus keep abreast of AI-related rulings as variations of the instant factual scenario may result in significantly more impactful decisions.
• Be thoughtful when utilizing AI. As daily AI-use proliferates, its use will have consequences. And, in the context of legal proceedings, those consequences can be serious, such as the destruction of privilege surrounding AI communications. Publicly available generative AI platforms in particular pose great risk as information entered as prompts most often does not remain confidential and ownership of its output is often unclear. It is therefore important to thoughtfully consider whether the use of AI will help or hurt any litigation strategy or impact regulatory investigations, and experienced counsel should be involved in all decisions and actions involving AI use in legal matters.

---

[1] February 10, 2026 minute entry, United States v. Heppner, No. 25-cr-00506-JSR (S.D.N.Y.) (“Heppner“); Dkt. 27 at 1–2, Heppner.

[2] Dkt. 27 at 4–12, Heppner.

[3] Id. at 2.

[4] Id. at 3.

[5] Id.

[6] Id.

[7] Id. at 3–4.

[8] Id. at 4.

[9] February 10, 2026 minute entry, Heppner; Dkt. 27 at 4, Heppner.

[10] Dkt. 27, Heppner.

[11] Id. at 5–8.

[12] Id. at 5.

[13] Id. at 5–6.

[14] Id. at 6.

[15] Id.

[16] Id. at 7.

[17] Id.

[18] Id.

[19] Id. at 7–8.

[20] Id. at 8.

[21] Id. at 9.

[22] Id. at 9–10.

---

Troutman Pepper Locke State Attorneys General Team

	Ashley Taylor – Co-leader and Firm Vice Chair Ashley is co-leader of the firm’s nationally ranked State Attorneys General practice, vice chair of the firm, and a partner in its Regulatory Investigations, Strategy + Enforcement (RISE) Practice Group. He helps his clients navigate the complexities involved with multistate attorneys general investigations and enforcement actions, federal agency actions, and accompanying litigation.
	Clay Friedman – Co-leader Clay co-leads the firm’s State Attorneys General practice and is nationally ranked by Chambers USA for AG Government Relations and in Best Lawyers for Advertising Law. He has dedicated his entire career to state attorney general and federal work, serving for nearly a decade in a senior role and more than 25+ years in private practice. Clay focuses his practice on helping industry-leading companies mitigate the risks associated with state and federal regulatory investigations and associated litigation.
	Chris Carlson Chris advises clients on regulatory, civil, and criminal investigations and litigation. With a background as an assistant attorney general, he provides practical guidance to clients with matters involving state attorneys general and federal regulatory agencies.
	Lauren Fincher Lauren has vast experience handling state attorneys general investigations, navigating complex regulatory compliance matters, and providing strategic counsel in enforcement actions across various industries. She helps clients manage high-stakes regulatory matters and guides them through complex legal landscapes.
	Stephen Piepgrass Stephen leads the firm’s Regulatory Investigations, Strategy + Enforcement (RISE) Practice Group, representing clients in single and multistate enforcement actions, including inquiries and investigations, as well as litigation involving state attorneys general and other state and federal governmental enforcement bodies. He has significant experience handling actions with federal agencies, including the CFPB and FTC, as well as single plaintiff and class action litigation for clients in highly regulated sectors such as financial services, health care, pharmaceutical, and education.
	Michael Yaghi Mike handles high-profile state attorneys general, FTC, and CFPB investigations by advising clients through these complex government inquiries. He assists clients through the entire life cycle of investigations, from regulatory enforcement through formal litigation.
	Matthew J. Berns Drawing on his experience in senior leadership roles in the New Jersey Attorney General’s and Governor’s Offices and as a trial attorney for the U.S. Department of Justice, Matt provides an insider’s perspective when guiding clients through complex government investigations, litigation, and other actions.
	Samuel E. “Gene” Fishel Gene is a former regulator with two decades of experience who has overseen state privacy and cybersecurity regulation enforcement, led national, multistate attorneys general privacy investigations, and prosecuted computer crimes at the state and federal levels. He has served at the forefront of state attorney general and federal enforcement, and utilizes this experience to proficiently represent client interests.
	Jeff Johnson Jeff helps clients navigate complex regulatory and litigation challenges with local, state, and federal authorities. His clients benefit from his decade of broad litigation experience, understanding of emerging state and federal regulatory issues, and strong relationships with attorneys general across the U.S. In addition to handling cases from trial through state or federal appeals, Jeff serves as amicus counsel in advancing legal rules to support his clients’ vital interests.
	Jay Myers Jay assists clients in heavily regulated industries, including health care, energy, insurance, emerging industries, and data privacy. He provides both regulatory legal advice and government relations strategies. Jay’s past and current clients include Fortune 10 companies, startups, nonprofits, industry associations, and advocacy groups. Recognizing that state government matters are often complex and multifaceted, he utilizes regulatory guidance, government advocacy, or both in tandem to deliver tailored solutions for each client’s unique needs.
	Zoe Schloss Zoe represents clients in litigation and government investigations. As former deputy attorney general for the Delaware Department of Justice, she is an experienced litigator who understands the enforcement priorities that impact her clients. Zoe works with individuals and corporate entities in highly regulated industries, including financial services, health care, and energy.
	Jessica Birdsong Jessica is an associate in the firm’s Regulatory Investigations, Strategy + Enforcement Practice Group. She received her J.D. from the University of Richmond School of Law, magna cum laude, where she served as associate articles editor of the Journal of Law & Technology.
	Nick Gouverneur Nick is an associate in the firm’s Regulatory Investigations, Strategy + Enforcement Practice Group. He received his J.D. from the University of Illinois College of Law, where he served as a member of the Journal of Law, Technology & Policy.
	Troy Homesley Troy is an accomplished litigator who has represented and defended clients across a wide range of complex, high-stakes disputes at both the trial and appellate levels. He has represented technology companies, business executives, law firms, investment funds, high-ranking federal officials, international non-profits, and asylum seekers. Troy draws on his broad litigation experience to advise clients before litigation arises, while claims are pending or threatened, and leading up to and through trial and appeals.
	Namrata Kang Namrata (Nam) is an associate in the firm’s Regulatory Investigations, Strategy + Enforcement (RISE) Practice Group, based in the Washington, D.C. office. She routinely advises clients on a wide variety of state and federal regulatory matters, with a particular emphasis on state consumer protection laws relating to consumer financial services and marketing and advertising. Nam’s experience transcends multiple industries, including financial services, telecommunications, media, and sports betting.
	Michael Lafleur Michael is an associate in the firm’s Regulatory Investigations, Strategy, and Enforcement Practice Group. Based out of the firm’s Boston office, Mike has deep experience in litigation, investigations, and other regulatory matters involving state-level regulators and state attorneys general.
	Philip Nickerson Philip represents clients in sectors such as financial, tech, real estate, and energy in a range of litigation matters. He is experienced in matters involving trade secrets, government investigations, commercial contracts, construction and product defect.
	Lane Page Lane specializes in federal and state regulatory investigations and complex civil litigation. He focuses on representing financial institutions and other businesses, with a particular emphasis on consumer protection and fair lending issues.
	Dascher Pasco Dascher is an attorney within the Regulatory Investigations, Strategy, and Enforcement practice, based in the Richmond office. She joined our firm after working in personal injury and medical malpractice for a Virginia trial law firm. Dascher brings varied legal experience to the firm with strong litigation and regulatory strategy capabilities.
	Kyara Rivera Rivera Kyara is an associate in the firm’s Regulatory Investigations, Strategy + Enforcement Practice Group. She received her J.D. from the University of Richmond School of Law, cum laude, where she served as publications and online editor of the Public Interest Law Review.
	Timothy Shyu Timothy is an associate in the firm’s Regulatory Investigations, Strategy + Enforcement Practice Group.
	Trey Smith Trey focuses his practice on representing and advising regulated utilities before state public utility commissions. He routinely helps clients obtain certificates of public convenience and necessity for transmission infrastructure. In this role, Trey works with his clients’ subject-matter experts to manage administrative proceedings, including by preparing initial filings; responding to discovery requests; drafting rebuttal testimony; and litigating any disputed issues.
	Daniel Waltz Dan helps clients navigate all aspects highly regulated relationships between industry participants and federal, state and local governments. Whether engaging with regulators, negotiating transactions or representing clients in the courtroom, he delivers solutions that help his clients achieve their strategic goals.
	Cole White Cole is a member of the firm’s Regulatory Investigations, Strategy and Enforcement (RISE) group. He has a decade of experience working in the attorney general community, having joined the firm from the Wyoming Office of the Attorney General, where he was assistant attorney general.
	Stephanie Kozol Stephanie is Troutman Pepper Locke’s senior government relations manager in the state attorneys general department.