Many people assume that a conversation with an AI chatbot is private — something between them and their screen, much like a diary entry or a personal note. A recent federal court decision shows that assumption can be dangerous, and potentially costly, for anyone facing criminal charges or involved in civil litigation.
The Case: United States v. Heppner
In February 2026, Judge Jed S. Rakoff of the U.S. District Court for the Southern District of New York issued a ruling in United States v. Heppner that sent a clear warning to anyone using consumer AI tools in connection with a legal matter.
Here’s what happened. After receiving a grand jury subpoena and learning he was the target of a federal securities and wire fraud investigation, the defendant, Bradley Heppner, began using the AI platform Claude, made by Anthropic. On his own initiative — without any direction from his defense attorneys — Heppner used Claude to organize his thoughts, generating roughly 31 documents that outlined potential defense strategies and analyzed the facts and legal issues he anticipated facing. He later shared some of these AI-generated materials with his lawyers.
When federal agents executed a search warrant at Heppner’s home, they seized his electronic devices. Those devices contained the AI-generated documents, which the government then sought to use as evidence. Heppner’s defense team argued the materials were protected by attorney-client privilege and the work-product doctrine, since they related to legal strategy and had eventually been shared with counsel.
The court disagreed — and its reasoning is worth understanding, because it applies well beyond this one case.
Why the Court Ruled Against Privilege
Judge Rakoff identified three independent reasons the AI-generated documents were not protected, any one of which would have been enough to defeat the privilege claim on its own:
1. Claude is not an attorney. The court explained that all recognized privileges require a trusting human relationship — specifically, in the attorney-client context, a relationship with a licensed professional who owes fiduciary duties and can be held accountable through professional discipline. No such relationship exists, or can exist, between a person and an AI platform.
2. There was no reasonable expectation of confidentiality. The court pointed to Anthropic’s privacy policy, which discloses that user inputs and AI outputs may be used to train the company’s models and may be shared with third parties under certain circumstances. Because Heppner had agreed to those terms, he could not reasonably claim his exchanges with Claude were confidential.
3. The documents were not created for the purpose of obtaining legal advice from an attorney. Heppner used Claude on his own volition, not at his attorneys’ direction. The court noted that Claude itself disclaimed the ability to give legal advice when asked. Sharing the resulting documents with his lawyers afterward did not retroactively convert them into privileged communications.
For similar reasons, the court also rejected the work-product argument. The work-product doctrine protects materials prepared by or at the direction of an attorney in anticipation of litigation. Because Heppner’s attorneys had not directed him to use Claude, and the documents did not reflect his attorneys’ own legal strategy, the doctrine simply did not apply.
Notably, the court left the door open on one point: had defense counsel directed Heppner to use an AI tool as part of building his case, the analysis might have come out differently. In that scenario, the AI tool could arguably have functioned as an agent of the attorney, similar to a paralegal or consultant working under counsel’s direction and protected accordingly.
Why This Matters Beyond Criminal Cases
Heppner arose in a criminal prosecution, but the underlying legal principles are not unique to criminal law. Attorney-client privilege and work-product protection operate the same way in civil litigation. If a party to a civil lawsuit uses a consumer AI platform to think through their case, organize evidence, or draft arguments — without the involvement of their attorney — there is a real risk that those exchanges could later be sought through discovery or a subpoena from the opposing party.
In short: whether you’re a criminal defendant, a civil litigant, or simply a member of the public thinking through a legal problem, treating an AI chatbot as a confidential sounding board can create a permanent, discoverable record of your private thoughts about your case.
A Practical Rule of Thumb
Based on the reasoning in Heppner, here is a simple guideline: never upload the following to a consumer AI platform without first speaking to your attorney:
- Police reports or incident reports
- Discovery materials received from the opposing party or the government
- Emails or communications with your attorney
- Witness statements
- Notes or thoughts about your legal strategy or defense
AI platforms like Claude and ChatGPT are excellent tools for general research, drafting, and organizing ideas. But they are not a substitute for your attorney, and they are not a confidential space to work through the facts or strategy of an active legal matter. Once information is typed into a consumer AI platform, you may lose the ability to argue later that it was ever private.
The Bottom Line
If you are facing criminal charges or are involved in a civil dispute, talk with your attorney before you talk to a chatbot about the facts of your case. What feels like a private conversation with a helpful AI assistant could, under the right — or wrong — circumstances, become evidence used against you.
If you or someone you know is under investigation or facing charges, don’t try to navigate it alone. Reach out, and let’s talk through your options.
Travis Sayre, Esq. 1130 Market Street Parkersburg, WV 26101 📞 304-893-9500 | 🌐 sayrelawservices.com
Serving Wood, Calhoun, Doddridge, Gilmer, Harrison, Jackson, Kanawha, Lewis, Marion, Mason, Pleasants, Putnam, Ritchie, Roane, Taylor, Tyler, Wetzel, and Wirt Counties. Serious felony cases accepted throughout West Virginia.
ATTORNEY ADVERTISING. For general informational purposes only. Not legal advice. Prior results do not guarantee a similar outcome. No attorney-client relationship is created by this post.