Recently, Judge Jed S. Rakoff of the Southern District of New York addressed what he called a “question of first impression” regarding AI logs. In United States v. Heppner, the court held that a criminal defendant’s conversations with the AI platform Claude were not protected by the attorney-client and work product privileges.
Matter of First Impression?
Perhaps, but Heppner merely applied core principles dating back to the nineteenth century. See Foster v. Hall, 29 Mass. 89, 101 (1831) (Citing, the “6th edition of that excellent work, Phillips on Evidence, published in 1824…”).
And earlier, Magistrate Judge Anthony P. Patti of the Eastern District of Michigan applied these principles quite differently in Warner v. Gilbarco, Inc.
Heppner and Warner Side-by-Side
| Warner v. Gilbarco, Inc., No. 2:24-CV-12333, 2025 WL 3047881 (E.D. Mich. Oct. 30, 2025) | United States v. Heppner, No. 25 CR. 503 (JSR), 2026 WL 436479, (S.D.N.Y. Feb. 17, 2026) | |
| Context | Civil: Pro se employment discrimination plaintiff used ChatGPT to draft litigation materials. Defendants moved to compel all AI-related documents and inputs. | Criminal: Defendant in securities fraud case used Claude (Anthropic) on his own initiative to prepare defense strategy reports after receiving a grand jury subpoena. Government moved for a ruling that seized AI documents were not protected. |
| Use | Pro se plaintiff used ChatGPT as a drafting and analytical tool during litigation preparation. She was effectively acting as her own counsel. | Represented defendant used Claude independently—without counsel’s direction—to generate reports analyzing facts, law, and defense strategy. He later shared the outputs with counsel. |
| Attorney-Client Privilege | Not directly at issue. Court addressed the motion on work-product grounds and did not need to reach a detailed privilege analysis for the AI materials. | Rejected on three independent grounds: (1) Claude is not an attorney—no attorney-client relationship; (2) communications not confidential—Anthropic’s privacy policy permits data collection, training, and third-party disclosure; (3) Heppner did not seek legal advice from Claude, which itself disclaims providing legal advice. |
| Work Product Doctrine | Protection upheld. Pro se litigants may assert work-product protection. AI inputs and outputs constituted internal analysis and mental impressions prepared in anticipation of litigation. Compelling disclosure would expose the litigant’s thought processes. | Protection denied. AI documents were not “prepared by or at the behest of counsel.” Heppner acted on his own volition, not as counsel’s agent. Documents did not reflect counsel’s strategy at the time of creation. Second Circuit requires a nexus to counsel’s mental processes. |
| Role of Counsel’s Direction | Not determinative. As a pro se litigant, Warner was effectively her own counsel. The court recognized her right to assert work-product protection over self-prepared litigation materials without any separate attorney direction. | Dispositive. Counsel conceded he “did not direct [Heppner] to run Claude searches.” Had counsel directed the work, Claude might have been treated as counsel’s agent (Kovel doctrine). Without that direction, the nexus to counsel’s mental processes was severed. |
| Waiver by Disclosure to AI Platform | No waiver. AI programs are “tools, not persons.” Work-product waiver requires disclosure to an adversary or in a manner likely to reach an adversary. Sharing with an AI tool does not meet this standard. | Confidentiality destroyed. Heppner had no reasonable expectation of confidentiality given Anthropic’s privacy policy allowing data collection, AI training, and disclosure to “governmental regulatory authorities.” This destroyed any privilege claim. |
| AI: Tool or Third Party? | AI = tool. “ChatGPT (and other generative AI programs) are tools, not persons, even if they may have administrators somewhere in the background.” | AI = third-party platform. Claude is operated by Anthropic, whose privacy policy permits data sharing. Users lack substantial privacy interests in conversations with publicly accessible AI platforms. Analogized to voluntary disclosure to a third party. |
| Relevance / Proportionality | Request denied as irrelevant and disproportionate under Rule 26(b)(1). Compelling a litigant’s internal drafting process was a “fishing expedition.” Defendants’ “preoccupation with Plaintiff’s use of AI needs to abate.” | Not at issue. AI documents were seized via valid search warrant during arrest. The question was purely whether privilege or work-product protection barred inspection—not discoverability. |
| Circuit Precedent | Sixth Circuit (broader view). Consistent with broad Sixth Circuit work-product doctrine. Cited Upjohn, One Tract of Real Property, and In re General Motors for the principle that even fact-based materials funneled through attorney analysis are protected. | Second Circuit (narrower view). Relied on cases holding that work-product doctrine’s purpose “is not generally promoted by shielding from discovery materials … prepared neither by the attorney nor his agents.” Cited In re Grand Jury Subpoenas, Gould, and Matter of Grand Jury Subpoenas. |
| Outcome and Reasoning | DENIED Defendants’ motion to compel AI materials. Reasoning: Work-product protection applies to pro se litigant’s AI-assisted litigation preparation. AI platforms are tools, not persons; using them does not waive protection. Defendants’ theory “would nullify work-product protection in nearly every modern drafting environment, a result no court has endorsed.” The pursuit was a “distraction from the merits” and a “fishing expedition.” Also denied as untimely and irrelevant/disproportionate under Rule 26(b)(1). | GRANTED Government’s motion; AI documents are not protected. Reasoning: Attorney-client privilege fails on all three elements. Work-product doctrine fails because documents were not prepared by or at counsel’s behest and did not reflect counsel’s strategy. Heppner acted independently. Non-privileged documents do not “alchemically” become privileged upon being shared with counsel. Respectfully disagreed with Shih v. Petal Card. |