Real Agent Cases

Work out which federal tax forms to file and how to fill them, line by line, with ChatGPT

Posted
by Gregory Lafrance (LinkedIn)
Last checked
Method:
How we verify

Evidence: Described by posterThe person describes what happened in words, without screenshots or video.

PartialThe source says it only partly worked, or had a significant problem a person had to deal with.

What went wrong: Helpful overall, but it swapped stock gain/loss numbers until he caught it.

Outcome

A filer gave ChatGPT a rundown of his W2, 1099 and business income, expenses and stock gains and losses, and asked which forms and schedules to use, in what order, with line-by-line instructions. He says it helped a lot with forms, sequence and deductions such as the self-employment tax deduction, but badly mixed up stock gains and losses numbers; he caught it, and ChatGPT admitted and fixed the mistake.

Agent

ChatGPT

Prompt Recreated prompt

The source didn't share its exact prompt, so we wrote this from what it describes.

Run this task now, exactly as written below. Everything you need is here, so start straight away and only stop if something required is missing or a rule below tells you to.

Goal: Tell me which tax forms and schedules I need, in what order, with line-by-line help.

Fill in before running:
- Income types: [W2 / 1099 / business / investments]
- Tax year and filing status: [DETAILS]
- Documents with personal ID numbers removed: [ATTACH]

Rules:
- List the forms and schedules and why each applies.
- Give the order to complete them and line-by-line instructions.
- Never switch or combine numbers silently; show each figure's source document.
- Flag anything that needs a tax professional or official IRS guidance.
- If a site asks for a login, a CAPTCHA or payment details, stop and hand control back to me.
- Ask for my OK before you pay, book, send, submit or cancel anything.
- Check facts that can change (prices, opening hours, dates, availability, rules) against the official source, and tell me anything you couldn't verify.

Output: A form list, completion order and line-by-line notes with sources.

You'll know it worked when: every number on the return traces back to a source document.
Optional stronger version

Our rewrite with extra checks. The poster didn't test it.

Run this task now, exactly as written below. Everything you need is here, so start straight away and only stop if something required is missing or a rule below tells you to.

Goal: Tell me which tax forms and schedules I need, in what order, with line-by-line help.

Fill in before running:
- Income types: [W2 / 1099 / business / investments]
- Tax year and filing status: [DETAILS]
- Documents with personal ID numbers removed: [ATTACH]

Rules:
- List the forms and schedules and why each applies.
- Give the order to complete them and line-by-line instructions.
- Never switch or combine numbers silently; show each figure's source document.
- Flag anything that needs a tax professional or official IRS guidance.
- If a site asks for a login, a CAPTCHA or payment details, stop and hand control back to me.
- Ask for my OK before you pay, book, send, submit or cancel anything.
- Check facts that can change (prices, opening hours, dates, availability, rules) against the official source, and tell me anything you couldn't verify.
- Before filing, check investment figures against your broker's tax forms yourself.

Output: A form list, completion order and line-by-line notes with sources.

You'll know it worked when: every number on the return traces back to a source document.

Before you finish: re-read my goal and constraints, check your answer against each one, and list anything you assumed or couldn't confirm.

Source

https://www.linkedin.com/posts/lafrancegreg_i-used-chatgpt-to-do-my-federal-taxes-initially-activity-7317775164706840576-JD7g

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