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Pay Contractors Through Square Payroll

Contractors must have their personal information completed before they can be paid. You can learn how to complete this information yourself in our Support Center.

Pay Contractors

  1. Log in to Staff > Payroll in your online SquareDashboard or Square Payroll app > click Pay Contractors.

  2. Select your pay period dates.Note: If you choose a pay period in a previous year, the payment will be included in the current year’s Form 1099-NEC.

  3. Choose your payment method. If you want to record a payment that has already been made or want to write checks for all contractors, choose Pay all Contractors by check.

  4. Select your contractor(s) and enter their pay or hours worked. If you are using Square Timecards (or a supported third-party timecards application) and/or Commission Tracking with Square Payroll, click Import time and wages to import your contractor’s hours and commissions for the pay period. Alternatively, you can manually enter commissions in the Amount column. 

    Note: Your contractor’s gross pay will be reported in Box 1 of Form 1099-NEC (nonemployee compensation).

  5. Click Continue.

  6. Review the contractor payment details and click Submit Payment.

  7. Contractors paid by direct deposit will receive pay 4 business days after you send the payment.

Delete a Contractor Payment

If your contractor was paid via manual check, you can correct and delete a historical contractor payment from your Payroll history.

To do so:

  1. Sign in to the History & Reports tab of the Square Payroll dashboard or Square Payroll app > select the specific pay period in question.

  2. Click Delete Payment > Confirm.

Deleted payments will not show up in the History tab and will not be included in form 1099-NEC at the end of the year. To delete all other types of runs, or if the contractors were paid via direct deposit, please contact us so we can help.

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