fyllyoA wash sale read as a full loss
A 1099-B shows a sale’s loss and, in a separate column, the part disallowed as a wash sale. Software that reads only proceeds and cost can report the whole loss, or carry the disallowed amount with the wrong sign.
TAX FORMS · IRS · BUILT IN
Fill Form 8949 with AISales and Other Dispositions of Capital Assets
Add the broker’s 1099-B, employee stock statements, old purchase confirmations and the client’s notes. Fyllyo fills Form 8949 on your Mac. Anything it can’t settle from the documents is left for you, with the reason.
Where AI form filling goes wrong on Form 8949
Form 8949 lists every sale from a broker statement, but the statement is rarely the whole story: a loss partly disallowed, a cost the broker never had, employee stock income already taxed as wages. Each row’s gain depends on reading the right figure from the right document. These are the common places AI tools and autofill get it wrong. What the form requires is for the IRS to say. Follow its instructions. IRS official page for Form 8949.
Employee stock with the broker’s basis
For employee stock plan shares, the 1099-B often shows only what the employee paid. The discount is already taxed as wages. Software that copies that basis can tax the same income twice.
A missing basis read as zero
For shares bought long ago or moved between brokers, the 1099-B often says the cost isn’t available. Software can read that as $0 and report the whole sale price as gain.
The client’s own gain figure
Clients often send a spreadsheet with their own gain or loss for each sale. Software that copies it can carry a mistake onto the form, such as a loss worked out before a wash sale.
The wrong box at the top of the page
Each part has boxes for whether a sale was reported on Form 1099-B and whether the basis was reported to the IRS, one box per page. Software can tick by holding period alone.
The offering date isn’t the date acquired
Employee stock statements carry an offering date and a purchase date. Software can take the earlier one as the date acquired, which can make a short-term sale look long-term.
How Fyllyo takes care of them
With a test client and five documents (a tax organizer, a consolidated 1099-B, an employee stock plan statement, a 2009 purchase confirmation and the client’s email with her spreadsheet), Fyllyo filled 38 fields in 19 seconds, each with the lines it came from.
- A wash sale read as a full loss. Adds the disallowed amount back as a positive adjustment with code W. In the test, a $2,400 loss became $800.
- Employee stock with the broker’s basis. Keeps the basis the broker reported and puts the difference from the plan’s adjusted basis in the adjustment column with code B. In the test, that was −750.
- A missing basis read as zero. Treats a missing basis as missing, not as zero. It reads the cost from the original purchase confirmation, including the commission. In the test, that was $3,960, not $0.
- The client’s own gain figure. Works out each gain itself from proceeds, basis and adjustments. In the test it got −800, where the client’s spreadsheet said −2,400.
- The wrong box at the top of the page. Reads each sale’s box from how the broker reported it. In the test, that was Box A for the short-term sales and Box E for the long-term one.
- The offering date isn’t the date acquired. Reads the date the shares were bought, as the broker and plan report it.
How much of a Form 8949 does Fyllyo fill?
Fyllyo can fill all 242 fields on Form 8949 from the client’s documents. Lines the documents don’t support stay blank and are listed for you to check.
You confirm on every form
- Taxpayer name
- Taxpayer SSN or identification number
- Total short-term gain or loss
- Taxpayer SSN or taxpayer identification number
- Total long-term gain or loss
What do you give Fyllyo?
Fyllyo reads the documents you already have. These can be PDFs, scans, photos, Word files or typed notes, and you can add several at once. Fyllyo works out which document answers which line.
Client data stays on your Mac
Client documents and the filled form never leave your computer. Fyllyo uploads nothing. Once it is set up, filling works offline.
What Fyllyo doesn’t do
Fyllyo doesn’t decide what to file, give legal or tax advice, or submit Form 8949 for you. Use the IRS’s official page for Form 8949 and your professional judgement. Fyllyo does the reading and the typing.
What if a document is a scan or a photo?
Fyllyo reads scans and photos as well as PDFs, Word files and typed notes. Clear, readable copies give the best results, and every answer on Form 8949 still shows the line it came from.
Fill your next Form 8949 on your Mac
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