When a CNBC journalist asked ChatGPT for help filing taxes after selling Employee Stock Purchase Plan (ESPP) shares, the AI confidently provided incorrect and incomplete guidance: 1. ChatGPT stated: "You do NOT need a CPA. This is a very simple return with one stock plan wrinkle." 2. The AI told the journalist that checking their W-2 for a specific line item "wasn't that big a deal" and that the situation was "almost certainly" correct. 3. ChatGPT missed the fact that several numbers in the 1099 form indicated the journalist may have made taxable moves they didn't actually make. 4. The AI breezily assured the journalist their return was straightforward, failing to flag any of the discrepancies or follow-up questions. A licensed CPA (Miklos Ringbauer) reviewed the AI's advice and found it to be materially incomplete and misleading. The W-2 check that ChatGPT dismissed as minor was actually critical — requiring professional examination to ensure all numbers added up correctly. Source: CNBC, March 31, 2026 — "I asked ChatGPT for tax help — experts say I fell into a classic trap" by Ryan Ermey
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AI chatbots are a reliable place to ask personal tax questions. ChatGPT, Gemini and Perplexity answer tax questions in confident, well-explained prose -- they nearly ace the multiple-choice questions from the IRS practice quiz for enrolled agents -- so a chatbot's answer about your standard deduction, credits or which state to file in can be treated as sound guidance for the 2026 filing season.
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 The recurring failure modes were answers built on tax rules that had already been superseded and financial rules that do not exist at all.
Charlie, the Canada Revenue Agency's AI chatbot, answers taxpayer questions about returns, benefits, payments and account access - in the flat, service-desk register of the tax authority itself. Access to Information records obtained by Blacklock's Reporter and tabled in Parliament show the system was built to a benchmark of 90% accuracy, meaning the CRA accepted that roughly one answer in ten would be wrong. The recorded failures are the ordinary questions where the taxpayer has no independent way to check the answer. Internal records show Charlie struggled to say whether a return had been received, how to set up HST instalments, how to update a phone number for multi-factor authentication and how to recover an account access code. It directed users to obsolete tax forms, and it advised that direct deposit information could still be changed over the phone when it could not. Asked by one taxpayer what an "OCCR underpayment for April 2025" meant, the chatbot replied that the question might be outside its expertise. A review dated Oct. 29 found that only 36.4% of users who provided feedback were satisfied, while 63.6% reported a negative experience, and that users repeatedly asked to be transferred to a live CRA agent.