I Used An AI Tool To Do My Taxes – Here's Where Experts Say I Went Wrong

The author typically has straightforward taxes but faced complexity after selling employee stock purchase plan shares for wedding funds, potentially triggering capital gains tax. Instead of consulting a tax professional, they decided to test AI assistance, joining the more than 20% of taxpayers planning to use AI for 2025 taxes. Using a paid corporate version of ChatGPT that wouldn't use their data for training, they uploaded their consolidated 1099 and received what seemed like helpful, easy-to-follow advice broken into bullet points. However, when double-checking with a CPA, they discovered the AI's guidance was flawed. The tax professional explained that AI models tend to give definitive answers when the reality is 'it depends,' and people often stop reading after getting the answer they want to hear. The number ChatGPT presented as 'almost certainly right' actually needed manual calculation and verification, and the AI missed problematic data in the 1099 because the user didn't know to ask about it. Tax professionals noted that large language models may be trained on outdated information that could be 9-18 months old or older, which is problematic given frequent tax law changes. For those using AI for taxes, experts recommend using thinking models rather than instant chatbots, being aware of data privacy policies, and always double-checking with tax experts, as the IRS won't accept 'the AI made me do it' as a valid excuse for mistakes.