AI bookkeeping for 1099 contractors: pick by the job you need done

"AI bookkeeping" means three different things depending on who's selling it. Some apps scan your bank feed for deductions and then file your return. Some keep your books and leave filing to you or your preparer. Some start from invoicing and add expenses so income and costs live in one place. The right one depends on which of those jobs you need done and who files your taxes.

The options, with prices from each company's site

Keeper's Business plan, at $1,199 a year, is for S corporations and partnerships, which is outside this comparison. Plans and prices change; the table reflects what each company showed on October 24, 2026.

What the IRS needs from your records

Whatever app you pick, the IRS says your supporting documents should identify the payee, the amount paid, proof of payment, the date and a description of what you bought or the service you received. Proof of payment alone, like a card statement line, doesn't establish that you're entitled to a deduction; you also need the receipt or invoice that shows you incurred the cost. Travel, gifts and car expenses need extra records. The law doesn't require a specific system, only one that clearly shows income and expenses. An app that categorizes bank transactions without receipts leaves half the job undone.

How AI reading works, and what you still check

AI receipt reading turns a photo into fields: vendor, date, total, tax, payment method and a suggested category. It's fast and usually close. It also misreads faded thermal paper, confuses subtotal and total on long receipts, and guesses categories from the vendor name. The useful apps show which fields they weren't sure about and make you confirm before saving. Treat the AI as a typist, not a bookkeeper. To see whether reading beats typing for your volume, the receipt entry time calculator runs the numbers with your own counts.

Matching bank deposits to invoices is the other half. A deposit of $2,400 from "HARLOW LLC" is easy to match to the $2,400 invoice for Harlow; two $500 deposits from clients with similar names aren't. Good matching explains why it paired a deposit with an invoice and never marks anything paid without your click.

Worked example: three contractors, three picks

Choose this if

In SoloWOS

In Expenses, Read receipt takes a photo (JPG, PNG or WebP), a PDF of up to 10 pages or, for Mexican invoices, the CFDI XML. A photo or PDF is read by Claude: vendor, date, total, subtotal, tax, payment method, a short summary and one of the expense categories (such as Software and subscriptions, Meals or Transportation and fuel). Unclear fields are marked in yellow, and nothing is saved until you click Save; the file stays attached as the receipt. On your phone, Take photo opens the camera. AI reads count against 5 a month on Basic, 300 on Solo and 900 on Team. SoloWOS's categories aren't Schedule C lines; see Schedule C expense categories to map them, or let your preparer do it from the CSV export.

In Invoicing, Match bank deposits takes your bank's CSV export, read without AI, or a PDF statement, read with AI and counted as one receipt read. It matches each deposit to an open invoice in the same currency by amount, invoice number and client name, says why ("Same amount, INV-0012 in the reference"), flags partial payments and possible duplicates, and marks invoices paid only when you click "Mark N invoices as paid". The statement file is read in memory and never stored.

The Taxes tab estimates what to set aside for each Form 1040-ES period from what you got paid and spent, with the code doing the math. SoloWOS doesn't file returns, doesn't pay the IRS and doesn't give tax advice; every estimate says so. Photos and PDFs go to Anthropic to be read; under Anthropic's commercial terms they aren't used to train their models. To start, log business expenses with receipts and send invoices clients pay by card; the SoloWOS AI assistant can also log an expense from a sentence. For the tax side, see whether AI can estimate quarterly taxes, and compare filing options in tax software for the self-employed. More in AI for freelancers.

Prices checked on October 24, 2026 on each company's own site.