Why now
Courts are drawing the line on client AI use.
Two decisions in 2026, one federal and one state, reached the same conclusion: when clients use public AI tools without attorney supervision, the conversations are discoverable.
Clients do not wait for permission to use AI. They paste demand letters, contracts, and their own account of a dispute into consumer chatbots, because the tools are helpful and free and always available. Until recently, nobody knew how courts would treat those conversations when the other side asked for them in discovery.
Now we are finding out.
Federal court, February 2026
United States v. Heppner
The United States District Court for the Southern District of New York ordered a criminal defendant to turn over his conversations with a public AI chatbot. He had used the consumer version of the tool to discuss his own pending case. No attorney was involved in the exchanges, and the service's consumer terms allowed the provider to retain the data, use it for training, and disclose it to third parties.
The court held that neither attorney-client privilege nor the work product doctrine protected the conversations. Privilege requires a confidential communication with counsel. A public chatbot, on consumer terms, is neither confidential nor counsel.
What the court examined
- Whether an attorney directed or supervised the AI use
- Whether the channel was confidential, including the provider's own data terms
- Whether the material reflected any lawyer's judgment or strategy
Massachusetts Superior Court, 2026
Shealy v. Seaside Investments
Months later, the Massachusetts Superior Court reached the same conclusion in a civil case. A represented plaintiff had a third party run his case documents through a public chatbot. His own counsel had no involvement. The court allowed the motion to compel, holding that neither the prompts nor the AI outputs were work product: they were prepared outside the representation and reflected no attorney's mental impressions.
“AI is a tool, not a person.”
Notably, the court distinguished federal decisions that extended work product protection to self-represented litigants using AI on their own behalf. The line courts are converging on is not whether AI was used. It is who was holding the tool, and whether the use happened inside a supervised representation.
What this means for intake
The question is not whether your clients use AI.
It is whether their AI use happens in a public tool their opponent can reach in discovery, or inside the representation, directed and reviewed by their lawyer.
CounselRoom is built around the factors the courts examined in Heppner and Shealy: firm-controlled access, attorney direction and supervision, and a record that shows both. It is designed to support privilege and work-product claims. No software can guarantee them, and anyone who says otherwise is selling something.
This page summarizes public court decisions in plain language, for general information. It is not legal advice. How these decisions apply to any matter depends on the jurisdiction and the facts, and the law in this area is developing quickly.
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