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NY Court Rules AI-Generated Documents Lack Legal Privilege
Attorneys must discuss AI use with clients due to risks of privilege waiver, experts say.
Mar. 16, 2026 at 1:00pm
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In a recent ruling, a New York federal judge determined that a criminal defendant's use of a consumer-grade AI tool to generate documents waived attorney-client privilege and work product protections. The decision in U.S. v. Heppner has lawyers across the country assessing the implications of AI use in legal defense.
Why it matters
The Heppner ruling highlights the risks attorneys and their clients face when using AI tools, as the technology's novelty does not exempt it from longstanding legal principles around privilege and work product. Lawyers must now have in-depth conversations with clients about AI use to avoid potential privilege waivers.
The details
In the case, defendant Bradley Heppner used the AI tool Claude after being subpoenaed and becoming aware he was the target of a criminal investigation. Judge Jed S. Rakoff ruled that Heppner's communications with the AI platform were not protected by attorney-client privilege or work product doctrine, as the documents were not created at the direction of his lawyers. The judge found the AI materials lacked key elements of privilege, such as confidentiality.
- In November 2025, FBI agents arrested Heppner and executed a search warrant at his home.
- On February 10, 2026, Judge Rakoff granted the government's motion to access Heppner's AI-generated documents.
- On February 17, 2026, Judge Rakoff issued a written opinion memorializing his bench ruling.
The players
Bradley Heppner
A criminal defendant accused of securities fraud and wire fraud related to his actions as an executive at GWG Holdings Inc.
Judge Jed S. Rakoff
The U.S. District Court judge who ruled that Heppner's use of the AI tool Claude waived attorney-client privilege and work product protections.
Alexandra N. Rothman
The Assistant U.S. Attorney who argued that Heppner's AI-generated documents were not protected by privilege.
What they’re saying
“AI's novelty does not mean that its use is not subject to longstanding principles, such as those governing the attorney-client privilege and the work product doctrine.”
— Judge Jed S. Rakoff (U.S. v. Heppner* opinion)
“Ultimately, this means that as lawyers, we must initiate much deeper conversations with our clients regarding both their use and our own use of AI on the matter before us.”
— Andrew W. Gregg, Shareholder, Bean Kinney & Korman (valawyersweekly.com)
What’s next
The judge in the case will decide on Tuesday whether or not to allow Bradley Heppner out on bail.
The takeaway
The Heppner ruling underscores the need for lawyers to proactively discuss AI use with clients, as the technology's novelty does not exempt it from established legal principles around privilege and work product. This decision highlights the evolving landscape around AI in the legal field and the importance of adapting practices to mitigate potential risks.
