1. Add the contractor as a vendor first. Go to Expenses > Vendors, then New vendor. Enter their name, email, and tax ID (SSN or EIN), and check Track payments for 1099. Skipping this step is the single most common reason a legitimate contractor payment doesn't show up on their 1099 later.
2. Decide how you're actually paying them. For a one-off or infrequent payment, a regular bill and check works fine. For contractors you pay regularly, QuickBooks Contractor Payments adds direct deposit, which most contractors prefer over waiting on a mailed check.
3a. To pay by bill and check: enter the bill. Click + New, then Bill, select the contractor as the vendor, add the expense line with the right category, and save. Then pay it through + New > Pay bills like any other vendor bill.
3b. To pay by direct deposit: use Contractor Payments. If you've added the Contractor Payments add-on, go to Payroll > Contractors, select the contractor, and choose Pay. Enter the amount, confirm their bank details are on file (they can add these themselves through a self-service invite), and submit the payment on QuickBooks' direct deposit schedule.
4. Confirm the payment landed under the right 1099 box. Whichever method you used, check the transaction is categorized to an expense account mapped to the correct 1099 box (usually Nonemployee Compensation, box 1 on the 1099-NEC) so it rolls up correctly when you run 1099 reports later.