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Fill Form 1099-S with AIProceeds From Real Estate Transactions

Add the 1099-S worksheet, the settlement statement, the purchase agreement, the sellers’ allocation and the seller’s certification. Fyllyo fills Form 1099-S on your Mac and shows the lines behind each answer for you to check.

Official form , instructions and page from the IRS.

Page 3 of Form 1099-S as Fyllyo filled it for a test client in a recorded run.
Page 3 of Form 1099-S, as Fyllyo filled it for a test client

Where AI form filling goes wrong on Form 1099-S

Form 1099-S is short, but every box sits next to a decoy in the closing papers. There are several dates and several money totals, and a seller’s old address is often the property itself. When a house has more than one owner, each owner’s own numbers sit beside the figures for the whole sale. 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 instructions for Form 1099-S.

What the seller took home isn’t the sale

A settlement statement ends with the cash paid to the seller, after the commission, fees and a loan payoff come out. That bottom line is the easiest number to find, and software often copies it as the proceeds.

One owner’s share, not the whole sale

When a property has two owners, each one gets a separate form, but the settlement statement shows the whole sale. Software can put the full price on each owner’s form, which doubles what’s reported.

Six dates for one closing

A sale has a contract date, a scheduled closing that can move, signing dates, a settlement date, a disbursement date and a recording date. Software often takes the first date it sees, or the one on the deed.

The property isn’t the seller’s address

A seller often lived in the house being sold, so the old papers give the property as the seller’s address. Software can put the property where the seller’s mailing address goes, or the seller’s new address where the property goes.

How Fyllyo takes care of them

With a test client and six documents (the title company’s 1099-S worksheet, a settlement statement, a purchase agreement with an amendment, a tax proration, the sellers’ allocation and the seller’s certification), Fyllyo filled 9 fields in 8 seconds. Each answer shows the lines it came from.

Fyllyo's review of a test Form 1099-S: gross proceeds filled as 242,500, this seller's allocated share, shown with the lines from the reporting worksheet and the sellers' allocation it came from.
  • What the seller took home isn’t the sale. Reads the gross amount for the sale before anything is taken out, never the seller’s net cash or a payoff.
  • One owner’s share, not the whole sale. Uses only the amounts written for this seller. In the test, that was 242,500, not the 485,000 price for the whole house.
  • Six dates for one closing. Reads the actual closing date from the final settlement statement, and skips signing dates, recording dates and a closing date that was later moved.
  • The property isn’t the seller’s address. Fills the property’s address from the closing papers, and the seller’s current mailing address from the seller’s own certification, never the other owner’s.

How much of a Form 1099-S does Fyllyo fill?

Fyllyo can fill all 15 fields on Form 1099-S 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

  • Transferor's TIN
  • Transferor's name
  • Gross proceeds

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 1099-S for you. Use the IRS’s instructions for Form 1099-S 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 1099-S still shows the line it came from.

Fill your next Form 1099-S on your Mac

Try form filling free for 5 days. Then buy Fyllyo Paid once for $99. It is a lifetime licence with free updates and no subscription. Filling forms on your Mac uses no AI credits. Pricing and licence details.