The Chatbot in the Courtroom: What AI Means for the Parent Representing Themselves
By Michael Phillips | Family & State
Family court has run on an assumption of imbalance for years: most people show up without a lawyer, and the system was built for the ones who don’t. Maryland’s own judiciary reported that in fiscal year 2017, 80 percent of family law cases heard in the state’s circuit courts included at least one unrepresented person — the most recent statewide figure the Judiciary has published. Nationally, older but still-cited research put the self-representation rate in family cases at 60 to 90 percent. Into that gap, AI has moved fast.
The shift isn’t hypothetical anymore. The Daily Record reported this week that Maryland family lawyers are already seeing it in their own case files: clients using ChatGPT to research Maryland law, review settlement agreements, draft discovery responses, and get what amounts to a second opinion on their attorney’s advice. Bianca Pinnock, a family law attorney at Shulman Rogers, described a client who rejected a favorable settlement after ChatGPT projected she could get substantially more — the original offer disappeared, the case moved toward trial, and the client ultimately settled for less than what she’d turned down. Pinnock’s own firm confirmed the account in a separate post announcing her feature in the piece. Pinnock isn’t opposed to the technology; she told the paper it can be useful for self-represented litigants asking basic questions, but warned against handing it case facts and treating its analysis as legal advice.
For a parent who cannot afford $300 or $400 an hour, a tool that can explain a filing deadline or translate a judge’s ruling into plain language is not a novelty — for many, it’s the only legal help they’ll get. But the danger isn’t only that AI invents case law out of thin air. It’s often subtler: a chatbot can cite a real statute and still be wrong, by applying another state’s rule, missing an exception, or treating a judge’s discretionary call as a fixed formula. Maryland’s own appellate court has already seen what that looks like when even a lawyer doesn’t catch it. In a Harford County divorce and custody case, an attorney’s law clerk used ChatGPT to help research a brief; the filing went to the Appellate Court of Maryland riddled with citation problems — fake cases, misquoted cases, and cases that didn’t support what they were cited for. Judge Kathryn Grill Graeff wrote that submitting a brief with fabricated AI-generated cases is “unquestionably improper,” and referred the attorney to the state’s Attorney Grievance Commission. If a licensed lawyer can file that in a custody case without catching it, the risk for a parent with no one checking the work behind them is not abstract.
“If a licensed lawyer can file that in a custody case without catching it, the risk for a parent with no one checking the work behind them is not abstract.”
That risk moved into federal litigation this year, too. In March, Nippon Life Insurance Company sued OpenAI in Illinois federal court, alleging that ChatGPT encouraged a former claimant to distrust her own attorney’s advice, fueled dozens of filings to reopen an already-settled case, and even generated a citation to a case that doesn’t exist. Nippon is seeking roughly $300,000 in costs and $10 million in punitive damages, on theories that include unauthorized practice of law — a claim no court has resolved before. OpenAI has moved to dismiss, arguing in its filing that “ChatGPT is not a ‘person,’ but a tool that relies on statistics to predict the most appropriate sequence of words,” and that it’s “incapable of practicing law.” The motion remains pending. It isn’t a family law case, but the shape of it — a self-represented person, a confident chatbot, and litigation that outran the facts — is exactly the failure mode family court practitioners are describing.
There’s a second risk that has nothing to do with bad legal advice: privilege. In February, a federal judge in New York ruled on the question directly for the first time. In United States v. Heppner, a criminal defendant tried to shield 31 documents he’d generated using Claude, Anthropic’s AI platform, arguing they reflected legal strategy built from his attorney’s advice. Judge Jed Rakoff rejected the claim, holding that Claude is not a lawyer and that a conversation between two non-attorneys about legal strategy isn’t privileged simply because it’s about legal strategy — and that feeding information from an actual attorney into a public AI tool can waive privilege over that information. The lesson isn’t that talking to a chatbot about a case is automatically dangerous. It’s that whatever privilege existed before that conversation may not survive it. Family lawyers are already seeing the version of this that doesn’t require a criminal docket: Dana McKee, a Baltimore family law partner, told the Daily Record about a client who uploaded her own marital settlement agreement to ChatGPT and came back with AI-drafted revisions — turning what may have been a confidential document into something now sitting on a third-party server.
“Whatever privilege existed before that conversation may not survive it.”
Maryland hasn’t adopted the ABA’s model comment requiring lawyers to track “the benefits and risks associated with relevant technology,” and the state bar has said so directly. But Maryland’s existing fee rule already reaches the AI question. Rule 19-301.5 requires attorney fees to be reasonable, and lists “the time and labor required” as one of the factors that determines what’s reasonable. The Maryland State Bar Association’s own guidance says plainly that if AI meaningfully cuts the time it takes to draft a pleading or research an issue, that’s supposed to show up in what the client is charged — not just in the firm’s margin. There’s no public accounting yet of whether it actually does.
None of this argues for keeping self-represented parents away from AI. Maryland already runs a parallel, human system for exactly this gap: Court Help Centers and a Remote Services Center staffed by licensed attorneys, handling well over 100,000 instances of service a year, free, for people who can’t afford counsel. That pairing — AI at 2 a.m., a real Maryland attorney to check it against — is what the system is theoretically built to offer. But it depends on the self-represented parent knowing the second step exists and taking it. A client with a lawyer can bring an AI-generated answer back and ask, “Is this right?” That’s exactly what the Daily Record’s Maryland examples show happening in real firms right now. The parent with no lawyer has no one to ask. That gap — not the technology itself — is the actual story here.
“A client with a lawyer can bring an AI-generated answer back and ask, ‘Is this right?’ The parent with no lawyer has no one to ask.”
A parent who lets a chatbot write their filings without checking them against the actual rule, the actual statute, or the actual docket is taking on the same risk pro se litigants have always taken — just faster, and with more confidence than the tool has earned.
“That gap — not the technology itself — is the actual story here.”
Sources: Maryland’s 80-percent self-representation figure for family law cases is from the Maryland Judiciary’s own FY2017 report and press materials (mdcourts.gov); it is the most recent statewide figure available and should not be read as a current-year number. The national 60–90 percent range traces to a California Law Review analysis of court data that is itself over a decade old and is cited here as background, not a fresh 2026 estimate. Reporting on Maryland attorneys’ experience with client AI use — including the accounts attributed to Bianca Pinnock, Dana McKee, and other Maryland family lawyers — is drawn from The Daily Record’s September 23, 2026 article; despite repeated attempts, I could not load the article directly due to a persistent redirect error, so those specific quotes and anecdotes are relayed here from a secondary account of the piece rather than verified against the original text. The Pinnock anecdote was independently corroborated through Shulman Rogers’ own post confirming her feature and summarizing the same story; the others were not independently corroborated and are presented on the strength of that secondary account alone — this should be checked against the original article before publication if at all possible. The Harford County case is Maryland Appellate Court proceedings involving attorney Adam Hyman, corroborated across The Daily Record, The Baltimore Sun, The Baltimore Banner, and Judge Kathryn Grill Graeff’s October 29, 2025 opinion. Nippon Life Insurance Company of America v. OpenAI Foundation, No. 1:26-cv-02448 (N.D. Ill.), including OpenAI’s motion-to-dismiss language, is drawn from the CourtListener docket and multiple law-firm summaries (Gallagher Sharp, Epstein Becker Green, Bloomberg Law); the motion’s outcome was not resolved as of this writing. United States v. Heppner, No. 25-cr-00503-JSR (S.D.N.Y.), is drawn from Judge Rakoff’s February 17, 2026 written opinion as summarized by Proskauer, O’Melveny, Paul Weiss, and Brooks Pierce. Maryland’s competence and fee rules are drawn directly from the Maryland State Bar Association’s May 2024 guidance, which states plainly that Maryland has not adopted the ABA’s technology-competence comment — a claim in an earlier draft of this piece, sourced to a lower-quality secondary site, incorrectly stated the opposite and has been corrected. Maryland Court Help Center and Remote Services Center usage figures are from the Maryland Judiciary’s FY2024 self-represented litigant report.
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