An HSA vs FSA prompt run cold: the AI reframed it as a choice between two health plans, then quoted a 2027 HSA limit $50 above the published one.
A ChatGPT prompt to size your September 15 estimated tax payment on $30,000 of 1099 income. The safe harbor came out to $465, not $7,500.
A ChatGPT prompt to choose Roth or traditional 401(k) in 2026, run on a $92,000 salary. The break-even retirement rate is 19.3%, not 22%.
OpenAI made free ChatGPT text chats unlimited on August 6, and Plus still bills $240 a year. Five checks that decide whether yours is now dead weight.
How to spot a value trap: run the four warning signs against free SEC EDGAR numbers. On one Nasdaq small cap, AI could answer just one of the four.