The newest, emerging technology impacting educational institutions, businesses, and now, courts. The increasing use of generative AI chatbots on websites like ChatGPT, Claude, Copilot, etc. have the courts on notice. Already, attorneys in Massachusetts have been sanctioned on multiple occasions for submitting to the court filings that contained fake cases, created by an AI website. (Dastou v. Holmes, 2025; Smith v. Farwell, 2024). Chatbots, like ChatGPT, will often “hallucinate” fictitious cases and laws when a user asks the bot to help draft a legal strategy. Using an AI chatbot can not only get your lawyer in trouble but could be the deciding factor in losing your case!
Warning About Using AI Even in the Background
Did you know that using AI could result in you losing an important privilege? Everybody knows about attorney-client privilege. Anything you and your attorney communicate to each other confidentially, stays confidential. But fewer people know about the work-product privilege. The work-product privilege is a legal rule that stops the opposing side from viewing and using your attorney’s notes, strategies, emails, thoughts, and conclusions about your case against you. Following previous decisions in New York and Michigan, the Honorable Debra A. Squires-Lee of the Suffolk County Superior Court issued an order addressing the use of AI and the work-product privilege in Massachusetts for the first time in the case of Shealy v. Seaside Investments this June 2026.
In the Shealy case, the main issue centered around a loan and whether the borrower properly paid off the loan on time. If the borrower did not pay back the loan on time, the lender would be entitled to shares in the borrower’s new company. A critical, and potentially fatal mistake was made when the borrower sent documents to his romantic partner, instructing her to upload them into ChatGPT, alongside some unknown prompt(s). While the borrower tried to argue that these prompts and responses by ChatGPT were created in anticipation of litigation and should be privileged as work-product, the judge disagreed. Justice Squires-Lee ruled that if a party is represented by an attorney, and their attorney did not instruct them to use the AI chatbot, any material produced by the AI chatbot for the party or a third-party non-representative is not protected under the work-product privilege. The Justice’s ruling allowed the opposing party to view all of the ChatGPT-related prompts and generated materials, potentially revealing sensitive information about the client, the loan, his representation, and his trial strategy.
In summary, BEWARE of using AI in litigation. Clients and attorneys both face new and increasingly harsh consequences for using these tools improperly. Always ask your attorney for legal advice, not an AI chatbot that could waive your privilege and give you an incorrect answer based on law that does not exist.
*This article was written by Alex Mathes, law clerk at Wilkinson & Finkbeiner, LLP. Alex Mathes | LinkedIn