Massachusetts Court Rejects Work Product Protection for AI-Generated Documents

A judge in Massachusetts just laid down a clear marker on AI and legal privilege: if your lawyer didn’t direct the AI search, your prompts and outputs aren’t protected.

The case—Shealy v. Seaside Investments, LLC—serves as a sharp warning for anyone using tools like ChatGPT to handle legal disputes on their own.

What Happened

In May 2025, after getting hit with a default notice over a commercial loan, Earl Wade Shealy Jr. wanted help drafting a response. Instead of calling his lawyer, he sent the documents to his romantic partner, Debbi Fields, who uploaded them into ChatGPT to analyze the deal and draft a reply.

When the dispute turned into a lawsuit, Shealy tried to redact his exchanges with Fields and the resulting AI output, claiming they were protected under the work product doctrine (which shields a party’s legal strategies and mental impressions prepared for trial).

The court disagreed and ordered him to hand over the unredacted documents.

Why the Court Rejected the Privilege Claim

• Romantic Partners Aren’t Legal Representatives: The work product doctrine covers materials prepared by or for a party’s attorney, consultant, agent, or insurer. Massachusetts law doesn’t treat romantic partners as legal representatives.
• ChatGPT Isn’t a Representative Either: The court ruled that an AI tool is simply software, not a person or an agent capable of forming protected “mental impressions.”
• No Direction From Counsel: Unlike recent federal rulings (Morgan v. V2X and Warner v. Gilbarco) where unrepresented (pro se) litigants were allowed work-product protection for AI prompts, Shealy actually had a lawyer—he just chose not to consult them.
• Zero Opinion Work Product: The court emphasized that without an attorney directing the prompts, AI output is just raw computer-generated text—it doesn’t reflect a lawyer’s strategic thinking.

The Bottom Line

Courts aren’t creating special, tech-friendly exceptions for AI. They are applying traditional attorney-client privilege and work-product rules strictly as written.

If you’re facing potential litigation and want your AI queries, prompts, and outputs shielded from the opposing side, your attorney must direct the process from start to finish. Otherwise, it’s all fair game in discovery.