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Check ESPP sales on a 1099 before filing with ChatGPT
PartialEvidence: Article or interviewPosted Last checked
ChatGPT explained Ryan Ermey's ESPP 1099, but a CPA found the advice incomplete and it missed some numbers.
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- Tap Copy prompt.
- Open ChatGPT.
- Paste it into the message box.
- Send it, then read the answer before acting on it.
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I sold shares from my employee stock purchase plan last year. Here's my consolidated 1099 from my brokerage. Explain how ESPP sales are taxed, whether the cost basis on this form is right, and what I need to change in my tax software before I file.
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Optional stronger version
Our rewrite with extra checks. The poster didn't test it.
Before you start, ask me 1–3 short questions about the details below and wait for my answers. Once I've answered, confirm the plan in one line and run the whole task start to finish. Goal: Check my tax forms for problems before I file, and list what a tax pro should confirm. Questions to ask me first: - Which forms do you have (1099, W-2, others), and for which tax year? - What did you sell or receive that you're unsure about? - Are you filing yourself, and with which software? Inputs (fill in or confirm): - Forms: [UPLOAD 1099 / W-2 PDFs] - Tax year: [YEAR] - What I'm unsure about: [QUESTION] Rules: - Go through every line with a number on the forms, not just the one I asked about, and flag anything unusual. - Explain which number goes into the tax software and why, and compare it with my W-2. - Don't call anything minor unless you explain why. - End with a list of questions to confirm with a CPA or enrolled agent. Checkpoint: After reading the forms, list every flagged line before giving advice so I can check it. If you get stuck: If a form is unclear or a number is missing, say so instead of guessing. Verify before you finish: Check that the numbers you quote match the forms exactly. Output: Flagged lines, what to enter in the software, and questions for a tax pro. Done when: I know what to enter and what to confirm with a professional before filing.
AI tool
Outcome
CNBC's Ryan Ermey asked ChatGPT how ESPP sales are taxed, then uploaded the consolidated 1099 from the brokerage, using a corporate version that doesn't train OpenAI's models. ChatGPT explained that the brokerage reports one number to tax software, but a different number has to be used, and said Ermey only needed to check a line on recent W-2s. Before filing, Ermey ran the chat by Miklos Ringbauer, a certified public accountant, who called it possibly correct but also incomplete. The W-2 check ChatGPT had played down was actually quite important. A few numbers on the 1099 also suggested taxable moves Ermey may not have made, and ChatGPT hadn't said anything about them.
Evidence: Article or interviewA newsletter, journalist or interview account of what happened.
Known limitations
PartialThe source says it only partly worked, or had a significant problem a person had to deal with.
What went wrong: The main explanation was possibly correct, but ChatGPT played down an important W-2 check and missed 1099 numbers that a CPA flagged.
Source
- Posted
- by Ryan Ermey (CNBC Make It)
- Last checked
- Method:
- How we verify
https://www.cnbc.com/make-it/2026/03/31/ai-tax-help-pitfalls.html
Context: Don't upload tax forms to an AI that trains on your data. Have a tax pro check the return.
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