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Re-do my taxes with AI and catch a bug in FreeTaxUSA itself

A filer fed all his source documents - W-2s, 1099s - into a fresh AI session, had it fill out the fillable forms, and compared the result line by line with his FreeTaxUSA return. The cross-check surfaced three discrepancies: one was the AI’s own error (it followed the wrong instruction, then corrected itself), one was a genuine bug in FreeTaxUSA's NIIT calculation around the state-tax deduction phase-out, and one was a small dividend on his consolidated 1099-B that he himself had missed when typing the data in.

This only partly worked. Read what happened before you try it.

How it works

  1. Upload all source documents to a fresh AI session
  2. Have it complete the fillable forms
  3. Compare against the FreeTaxUSA return
  4. Investigate the three discrepancies (one AI error, one software bug, one missed dividend)

Why it’s worth knowing

The verification ran three ways: the agent caught the tax software's bug and the filer's own missed dividend - and got caught making one error itself.

Where it’s from

Summarized from a public post on reddit.com. See the original ↗

Upgraded prompt

A ready-to-use prompt for this idea, built from research on what makes AI agents do the job right: who the AI should be, the exact steps, and a check to make sure it was done the way you wanted.

1Who the AI should be
2The prompt, with the steps
3The check when it’s done
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