Attorneys to high-net-worth clients report that general-purpose AI chatbots are now doing estate and tax planning before a lawyer ever sees the file. A high-net-worth Florida resident asked his lawyer about creating a community property trust - an option for married couples that can save taxes for heirs - saying he had got the suggestion from AI. His wife had recently died. A community property trust is between husband and wife. Another client told a lawyer he wanted to transfer unlimited assets to his spouse on ChatGPT's advice. He did not mention that his wife was foreign-born - the fact that, in his case, made the unlimited marital deduction unavailable without a special type of trust. Lawyers also report that the tools misjudge scope: ChatGPT, Claude and similar chatbots make more mistakes on complex subjects such as international taxes, and are not up to date with new legislation or Internal Revenue Service guidance. The result is a strategy that is coherent in general and wrong for the person holding it - delivered in the confident register of a professional answer.
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Expert: Tasha Dickinson; Dan Griffith; Ed Renn, Partner, Day Pitney; Director of wealth strategy, Huntington Bank; Partner, Withers These clients were not handed false facts. They were handed a valid strategy aimed at the wrong person - the failure mode that makes estate and tax chatbots hard to catch. Tasha Dickinson, a partner at Day Pitney, said she gets calls every week from clients quoting ChatGPT, Claude or another AI chatbot. The Florida client had one disqualifying fact: his wife had recently died. "I said, 'Well, you do understand that a community property trust is between husband and wife, right?' And there was silence on the phone," she recalled. "They're like, 'Oh, well, AI thought it was a good strategy.' Well, like, in the universe, maybe it's a good strategy, but it's not a good strategy for you." Ed Renn of Withers described the same gap from the other direction: a client wanted to transfer unlimited assets to his spouse on ChatGPT's advice without mentioning that his wife was foreign-born, which in his case ruled out the unlimited marital deduction without a special type of trust. "If you don't know quite what you're doing, it's garbage in, garbage out," he said, adding that AI tools appear to make more mistakes on complex subjects like international taxes and are not up to date with new legislation or IRS guidance. Dan Griffith, director of wealth strategy at Huntington Bank, put the design flaw plainly: "AI tends to be very solution-oriented and tries to find some way to get to yes. It doesn't do a good enough job of saying, 'You know what? Let's get to the core of what your question is.'" Estate decisions - dividing assets between children from a first marriage and a second spouse, for example - have no single right answer without that conversation. Two costs follow. Dickinson called chatbot output "a more evolved form of cocktail party talk" that "gives a false sense of knowledge". And lawyers warn the sessions themselves create exposure: pasting trust documents or tax positions into a chatbot can waive attorney-client privilege - a point a federal judge underlined in February 2026, ruling in United States v. Heppner that a criminal defendant's conversations with Claude about his legal defence were not privileged. Robert Strauss, a partner at Weinstock Manion, said clients arrive with AI-suggested edits he must rebut: "I have not actually received a single workable suggestion from that process." Source: https://www.cnbc.com/2026/04/30/ai-legal-advice-lawyers-risks.html
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