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Sanity-check investment tax forms before you upload them
Ops & admin automation · checked 2026-10-17
Have Gemini summarize a redacted broker 1099-B (total proceeds, cost basis, gain or loss direction) so you know what to expect, then upload the original 1099-B or Form 8949 to FreeTaxUSA and confirm the totals match.
Independent review. IonBin has no partnership with any tool on this page and was not paid for this page. Our evaluation is our own, based on public documentation and our research. Product names are trademarks of their owners and are used for identification only. How disclosure works.
Goal
Catch a wrong-direction gain or loss before it reaches your return.
Connects through: Upload / export
Not advice
IonBin provides general information and software comparisons, not tax, legal, accounting or financial advice. Tax and legal rules vary by situation and jurisdiction; consult a qualified professional (CPA, enrolled agent or attorney) before acting.
AI tools can make mistakes. Verify every figure against the original documents and official IRS or state guidance before filing or signing.
Redact Social Security numbers, account numbers and EINs before uploading documents to any AI assistant, and check its data-retention settings. Upload originals only to the filing or signing software.
“Free” offers come with conditions: check who qualifies and what state filing costs before you start. IRS Direct File is discontinued for the 2026 season with no relaunch date; see IRS Free File for eligible filers.
Steps
#
Who
What happens
How
Status
1
You
Redact account numbers and personal identifiers on the broker’s 1099-B
Confirm the imported totals match the broker form and the summary, then continue your return
Human step
Confirmed
Confirmed means the vendor documents it (linked). It doesn't mean IonBin has tested it. AI-platform and human steps need no source.
Human approval
You confirm totals against the broker form. Gemini’s summary is a cross-check only.
Watch out for
Keep the human approval step: You confirm totals against the broker form. Gemini’s summary is a cross-check only.
Starter prompt
Goal: Catch a wrong-direction gain or loss before it reaches your return. Tools involved: Gemini, FreeTaxUSA. Your part: summarizes the redacted form: totals by term, overall gain or loss, and any wash-sale adjustments shown. Work step by step, show me each draft or proposed change, and wait for my approval before anything is sent, published, signed, filed or changed in a live system.
Assembled from this page’s goal and steps. Paste it into your AI platform and adjust it to your situation.
No platform-specific connection: the steps run in the tools themselves (browser, upload or built-in).
ChatGPT
Confirmed
No platform-specific connection: the steps run in the tools themselves (browser, upload or built-in).
Gemini
Confirmed
No platform-specific connection: the steps run in the tools themselves (browser, upload or built-in).
Perplexity
Confirmed
No platform-specific connection: the steps run in the tools themselves (browser, upload or built-in).
Computed from the MCP and API steps only: "Confirmed" needs the tool's docs to name the platform and the platform to support the connection. Browser, upload and human steps work from any platform.
What we checked
FreeTaxUSA lets you e-file a copy of your 1099-B or Form 8949 and upload 1099-Bs to verify your overall loss or gain. It doesn’t say how it handles a multi-page consolidated 1099 from a broker (1099-B, 1099-DIV and 1099-INT in one PDF). After uploading one, check that every section came through, not just the first.
Pricing. FreeTaxUSA lists $0 for a federal return and $15.99 for a state return, for 2025 returns (checked 2026-10-17).
Gemini’s role is a cross-check. It reads only the redacted copy and gives you totals to expect, so a wrong-direction gain or loss stands out.
Set it up
Download the broker’s tax form as a PDF and make a redacted copy (remove account numbers, your SSN and address).
Ask Gemini for total proceeds, cost basis and gain or loss, split by short and long term, plus any wash-sale adjustments the form shows.
Upload the original to FreeTaxUSA.
Compare FreeTaxUSA’s totals with the broker form and Gemini’s summary. If they differ, the broker form wins: re-check the import, not the form.
