Asked how much of a home sale is exempt from capital gains tax, ChatGPT and Claude got the answer wrong about two-thirds of the time in a Loyola University Chicago test. In one real case, a chatbot wrongly assured a taxpayer they did not need to report crypto income under $3,000 — the IRS disagreed.
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Expert: Keela Robison, VP of Product Management, Intuit AI chatbots gave confidently wrong tax answers when Bloomberg reporters and researchers put them to the test. A Loyola University Chicago study asked chatbots a simple question — how much of a home sale is exempt from capital gains tax — and they got it wrong about two-thirds of the time. In one case cited by tax experts, a chatbot wrongly assured a taxpayer they did not need to report crypto income under $3,000; the IRS disagreed. “ChatGPT is really good at telling you what you want to hear,” one tax expert told Bloomberg. Keela Robison, VP of Product Management at Intuit, said: “Right now, we do not feel that LLMs can process taxes, certainly not complicated taxes.” Experts also warn that chatbots misread digits on tax documents and give misinformed advice. The risk is growing: a new Adobe survey found 26% of U.S. workers plan to use AI to help file their taxes this year, up from 11% last year. The expert consensus: treat AI as a brainstorming tool, but verify every figure and rule against official IRS guidance or a licensed tax professional before filing. Source: https://www.entrepreneur.com/business-news/chatgpt-or-claude-to-file-your-taxes-use-caution
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Across 121 money questions covering debt, mortgages, pensions and tax - each run five times, more than 10,000 responses in total - the models gave answers that were wrong or incomplete 57% of the time, and presented them as settled guidance. On the hardest multi-step questions the failure rate reached 88%. Gemini 3.5 Flash and Claude Haiku 4.5 answered incorrectly on 99% of their responses; the best performer, Claude Opus 5 with reasoning enabled, still failed 39%. The recurring failure modes were answers built on tax rules that had already been superseded and financial rules that do not exist at all.
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