Fill Out Form 8949 in Seconds with AI

Upload your Form 8949, and Simplicity AI fills in transaction details, asset descriptions, proceeds, cost basis, and gain/loss calculations automatically. Whether you have one sale or hundreds, stop manually typing the same information.

AI converts your 8949 into a smart, interactive form. No misaligning numbers or squinting at tiny boxes.

Upload brokerage statements or 1099-B forms as source documents, and AI pulls each transaction straight into the 8949.

Reporting hundreds of sales? Auto-fill each transaction from your records. Same accuracy, much faster than manual entry.

Form INFORMATIONS

Part I – Short-Term Transactions:

Report assets held for one year or less. Include the description of the property, date acquired, date sold, proceeds, cost basis, adjustments, and gain or loss. Accurate reporting ensures your short-term capital gains tax is calculated correctly.

Part II – Long-Term Transactions:

Report assets held for more than one year. Include the same information as Part I. Properly separating short-term and long-term transactions prevents miscalculation of taxes.

Column A – Description of Property:

Enter the name of the asset sold, such as stock, bond, or mutual fund. Include account numbers if applicable for identification.

Column B & C – Dates:

Enter the date you acquired the asset and the date it was sold. Incorrect dates may trigger IRS notices or misclassify the holding period.

Column D & E – Proceeds and Cost Basis:

Enter the total proceeds received from the sale and the original cost or other basis. Accuracy here is critical for calculating correct gains or losses.

Column F – Code:

If adjustments are needed (for example, wash sales), enter the appropriate IRS code.

Column G – Adjustments:

Enter any adjustment amounts to gain or loss. This could include disallowed losses or fees.

Column H – Gain or Loss:

Automatically calculated as Proceeds minus Cost Basis plus or minus Adjustments. Ensures accurate reporting to Schedule D.

Summary:

Totals from Part I and Part II feed directly into Schedule D of your tax return, which calculates overall capital gains or losses.

WHAT IS FORM 8949?

What Is Form 8949 and Who Needs to File It?

IRS Form 8949, officially called "Sales and Other Dispositions of Capital Assets," is how taxpayers report gains or losses from the sale of stocks, bonds, mutual funds, or other capital assets. You must file Form 8949 if you sold any capital assets during the tax year.

Unlike your brokerage statements or Form 1099-B, which report raw transaction data, Form 8949 organizes, adjusts, and summarizes transactions for accurate reporting to the IRS.

If any of the following describe you, you need to file Form 8949: You sold stocks, bonds, or other securities during the tax year. You sold mutual funds or ETFs and received proceeds from your brokerage. You need to report adjustments, such as wash sales, to accurately calculate gains or losses.

The form may appear long, especially for multiple transactions, but calculating gains and losses, applying adjustments, and summarizing totals can get tedious quickly. That's where Simplicity AI comes in.

How to Fill Out Your 8949 Online in 6 Simple Steps

Upload your Form 8949 PDF to Simplicity AI. The AI scans the form layout, detects transaction fields, and converts it into a guided questionnaire.

Enter your personal information: name, SSN, and address. This links your transactions to your tax return.

Upload brokerage statements or 1099-B forms. AI extracts transaction details, including asset description, dates, proceeds, and cost basis.

Enter any adjustments, such as wash sales or fees. AI maps codes and automatically adjusts amounts to the correct columns.

Review all transactions to ensure accuracy. Verify dates, proceeds, cost basis, and gains/losses. Small errors can trigger IRS audits or notices.

Export your completed Form 8949 as a clean PDF. Submit with your tax return or electronically where allowed. Keep a copy for your records.

Super Fast

Complete each Form 8949 in minutes, even with hundreds of transactions.

AI-Powered

Simplicity AI understands the 8949 structure and maps each transaction to the right columns.

Secure

Your forms contain SSNs, account numbers, and financial transactions. Documents are encrypted and never shared.

FAQs

FORM 8949: Frequently Asked Questions

Who needs to file Form 8949?

Anyone who sold capital assets, including stocks, bonds, or mutual funds, during the tax year.

How do I fill out Form 8949 online for free?

Upload your Form 8949 PDF to Simplicity AI. The platform converts it into a guided, interactive form. Enter transactions, adjustments, and review totals. Export a clean PDF when complete.

When is Form 8949 due?

Form 8949 is filed alongside your tax return, usually by April 15. Late or incorrect filings may affect your capital gains calculations or trigger penalties.

Can I file multiple 8949s at once?

Yes. If you have multiple brokerage accounts or hundreds of transactions, AI can auto-fill each 8949 accurately using uploaded statements.

Is my data secure?

Yes. Form 8949 contains SSNs, account numbers, and financial transaction data. Simplicity AI encrypts all documents and keeps your information private.

Common Mistakes When Filing Form 8949
(and How AI Prevents Them)

Incorrect Dates

Reporting the wrong acquisition or sale date can misclassify gains as short-term or long-term. AI extracts dates directly from your statements.

Proceeds or Cost Basis Errors

Mistakes here miscalculate gains or losses. AI auto-fills these values from source documents.

Forgetting Adjustments

Wash sales, fees, or disallowed losses must be entered. AI ensures proper codes and adjustment amounts are included.

Mixing Short-Term and Long-Term Transactions

Misreporting can result in incorrect tax calculations. AI automatically separates Part I and Part II.

Failing to Summarize Totals Correctly

Totals feed into Schedule D. AI calculates totals accurately, preventing manual miscalculations.

Not Keeping Source Documents

Brokerage statements must be retained. AI integrates them as source documents for verification.

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