thread Re: How do I pay taxes? in Staff & Payroll

How do I pay taxes?

khenderson — Sun, 21 Sep 2025 06:56:23 GMT

I just started the square payroll. I made a 2-week payment in January without using square, but I did calculate taking all the appropriate taxes out. Then I started making weekly payments the last 2 weeks in July through square. How do I submit the monthly payroll taxes for January showing the first two weeks payment through mytax.illinois.gov?

Re: How do I pay taxes?

AshleyK — Wed, 05 Feb 2020 23:05:22 GMT

Hey there!! You can utilize a free off-cycle payment to get caught up! You will have to process one regularly scheduled payroll run first though.

To make an off cycle payment:

Log in to the Payroll section of your online SquareDashboard or Square Payroll app > Pay Employees > Off-Cycle Payment.
Select the Pay Period you would like to pay your employee(s) for, or define a custom period.
Select the Payment Type that applies to the payment. Selecting Regular Pay will calculate taxes based on the tax rates and W-4 information at the time the off-cycle payment is sent. If you’re sending a bonus, select that Payment Type and taxes will be calculated using the supplemental withholding rate. To learn more about withholding rates, refer to IRS Publication 15 and your state’s employer’s tax guide.
Select the Payment Method you would like to use to pay your employee(s). You can pay all employee(s) by their default payment method or by check.
Select the employee(s) that you wish to pay and enter the number of hours worked and any additional pay for each employee. If you’re using Square Point of Sale’s timecards or a supported third-party timecard application, click Import Timecards to import your employee’s hours worked for the pay period.
After entering in this information for all employees that need to be paid, click Continue.
You will be taken to the Adjustments screen where you can add reimbursements if needed. If you’ve set up employee benefits or post-tax deductions, you can also confirm deduction/contribution amounts and make any necessary edits. Once complete, click Continue.
You will be taken to the Review screen containing a detailed breakdown of the off-cycle payroll and bank withdrawal. Click Confirm Withdrawal to approve and process the off-cycle payment(s).

Note: If you make an error, you have until 7 PM PT that evening to cancel your off-cycle payment using the Cancel. To confirm that your off-cycle payment has been successfully processed, you must confirm it’s reflected in the History tab of your Square Payroll dashboard.

Re: How do I pay taxes?

LaurenSQ — Thu, 06 Feb 2020 15:39:05 GMT

Hi @khenderson welcome to Square Payroll! 🎉

The off-cycle payment option works well if you have not made any tax payments to your state tax agency or IRS and only issued checks to your employees for their net pay. If this is the case, processing an off-cycle payment is a good option - when processing the off-cycle payment, you will want to select the option to "pay all employees by check" so they are not paid a second time, via direct deposit.

With that being said, if you have already paid the taxes for the run that you processed prior to starting with Square Payroll, you will want to email us your prior payroll history instead of running the off-cycle payment. You can contact Square Payroll at payroll@help-messaging.squareup.com and the Square Payroll tax team will enter this information on your account to include it on the 2020 W-2s.