The foundation of 1099 reporting starts when you first hire a contractor, not in January. Before you pay anyone for services, collect a W-9 form from them. This form captures their legal name, address, and tax identification number. Chasing down W-9s after the fact is frustrating and sometimes impossible when contractors have moved on to other work or changed their phone number.

Track every payment to each contractor throughout the year. Your accounting software should categorize contractor payments so you can pull a report showing exactly who received what. If you pay a contractor $600 or more during the calendar year for services, you must send them a 1099-NEC form. Monthly bookkeeping that properly categorizes these payments means the information is ready when you need it.

The $600 threshold applies to services, not products. Buying materials from a supplier doesn’t trigger 1099 reporting. Payments made through credit cards or payment apps like PayPal and Venmo don’t require a 1099-NEC from you either because the payment processor handles that reporting. Cash and check payments to contractors are where your reporting obligation kicks in.

1099-NEC forms must reach contractors and the IRS by January 31. No extension exists for this deadline. Penalties for late filing start at $60 per form and increase based on how late you file, reaching $310 per form if you file after August 1. Intentional disregard of the requirement pushes penalties even higher.

Filing is straightforward if you’ve kept good records. You can file paper forms with the IRS or e-file through the IRS FIRE system or third-party services. E-filing is required if you’re submitting 10 or more 1099 forms. Most accounting software can generate the forms directly from your contractor payment records.

Arkansas participates in the Combined Federal/State Filing Program, so when you e-file with the IRS and indicate Arkansas, the state receives the information automatically. One less thing to worry about.

Common mistakes include forgetting about smaller contractors who crossed the $600 threshold late in the year, omitting reimbursements that should have been included, and misclassifying employees as contractors. That last one creates serious problems beyond 1099 reporting. If the IRS or state determines someone you treated as a contractor was actually an employee, back taxes and penalties follow.

Working with a bookkeeper near Fayetteville who tracks your contractor payments throughout the year means January becomes a simple reporting task instead of a stressful research project. The W-9s are on file, payments are categorized correctly, and generating 1099s takes minutes instead of hours.