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Lessons from a case where a defendant's claim of legal privilege over AI documents failed.
In United States v. Heppner, Judge Jed S. Rakoff of the U.S. District Court for the Southern District of New York ruled that documents created by a defendant using a third-party AI tool are not protected by attorney-client privilege or the work-product doctrine, even when later shared with lawyers.
The case involved Bradley Heppner, who faced securities and wire fraud charges. Before his arrest, Heppner used Anthropic's AI assistant Claude to generate approximately 31 documents analysing the government's investigation. He then emailed these documents to his legal team. When federal agents later seized the materials, defence counsel argued they were privileged.
Judge Rakoff disagreed. Applying established legal privilege principles to an AI context, he concluded that:
- AI tools are not lawyers, so communications with them do not qualify as privileged;
- Heppner had no reasonable expectation of confidentiality given the AI tool's data-collection practices and privacy terms;
- Sharing AI-generated content with a lawyer after the fact does not retroactively create privilege; and
- The work-product doctrine did not apply because the materials were not created at the direction of counsel.
The ruling serves as a clear warning: using consumer AI tools independently for legal purposes may expose sensitive materials to discovery.
How to protect legal privilege when using AI
Although this decision specifically addresses a defendant's use of a publicly available AI platform in connection with a pending criminal investigation and is silent on the position of the use of enterprise AI platforms, it represents one of the first rulings on this issue and offers valuable guidance. Individuals and organisations using AI in legal contexts should consider the following precautions at a minimum:
- Avoid using public AI tools for confidential legal matters: Consumer-grade AI platforms with broad data-use terms pose significant risks.
- Use enterprise-grade or privacy-protected AI solutions: Use platforms with explicit contractual guarantees of confidentiality and restrictions on data use.
- Ensure counsel directs any AI use: Where AI is used in connection with privileged legal work, ensure that a suitably qualified lawyer provides explicit guidance on the appropriate use of the tool, that such use is conducted under the lawyer's instructions, and that this direction is documented contemporaneously.
- Clearly mark privileged AI-assisted communications: When appropriate, note in prompts and logs when AI outputs or prompts are created at the instruction of counsel for legal strategy.
- Review privacy policies in advance: Understand and document the privacy and data-handling policies of any AI service before entering case-related information.
Why understanding the law and AI matters
As the Heppner ruling shows, the way AI is used and who supervises that use, has significant consequences in litigation and privilege assessments. As an emerging field, specialist expertise are required in order to:
- Select the right AI tools by distinguishing between consumer AI and enterprise platforms offering confidentiality protections.
- Integrate AI safely within workflows that align with legal privilege requirements and avoid inadvertent waiver.
- Document matters properly, ensuring records reflect lawyer direction and purpose where privilege is at stake.
- Anticipate discovery risks and develop strategies that minimize the risk that AI-generated materials will be used against a client.
With AI rapidly becoming part of legal workstreams all over the world, including the African continent, the Heppner ruling is a timely reminder on how traditional privilege doctrines intersect with modern technology. Thoughtful, well supervised use of AI can help preserve confidentiality in a world where digital tools are increasingly part of professional practice.
How ENS intelligENS Can Help
ENS intelligENS is our specialist legal technology and AI division, comprising lawyers, data scientists and technologists who combine legal expertise with technical fluency. Our team brings a deep understanding of both AI systems and the legal frameworks governing their use, including in complex matters such as criminal investigations, securities litigation, fraud proceedings, and regulatory inquiries. The very contexts at issue in the Heppner ruling. We advise on AI governance and assist clients in incorporating AI-generated work into legal disputes, regulatory responses, and investigative workflows whilst preserving privilege. Reach out to ENS intelligENS to learn how we can support your organisation in navigating the evolving intersection of artificial intelligence and legal practice.
The content of this article is intended to provide a general guide to the subject matter. Specialist advice should be sought about your specific circumstances.
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