Windward Payroll Update 2022

Windward Software has updated Windward System Five's Payroll Module to incorporate tax changes for 2022. By updating your Windward Payroll module you will ensure payroll calculations are accurate. Windward Payroll is now available for the following regions:

  • Canadian rates now available for Alberta, British Columbia, Manitoba, New Brunswick, Nova Scotia, Ontario, Saskatchewan (STILL IN TESTING: NL; JUST IN BETA TESTING: YT)
  • United States rates available for Michigan, Oklahoma, Maryland, Wisconsin (STILL IN TESTING: NC, IL, LA, MT, TX)
If you are not running Windward Payroll, you do not need to apply this update. This process is for on-premise installations of Windward System Five. If you are a System Five on Cloud customer contact Customer Care to schedule an update.


Windward Payroll version should be with a System Five version of from October 21 2021 or greater.

If your Windward Payroll version is not up to date, you can choose to update just payroll using the ftp update process. You can also call support to schedule an appoint or you can visit us online to schedule an Online Booking Appointment.

How to Update PayrollSYS files

The S5 Payroll downloader provides an easy way to update your tax tables. This article will give you step-by-step instructions to update your payroll tax tables. Use this process to apply the most recent PayrollSYS files to your Windward System Five datasets.

  1. NOTE: You may receive a security notification
    Ensure the program is published by Windward Software Systems Inc. and click on “Run”.

  2. Windward Payroll System Five Updater window will show up. Click on “Download Payroll.

  3. Download Complete should appear right below the 'Download Payroll' button. Then click on “Extract”.

  4. Choose the drive where Windward Payroll is installed and click on 'Search'.

  5. Ensure you have selected the correct path of bin location and click on 'Replace'.

    NOTE: The checkboxes changing to grey indicates the copy is completed.

Checking Windward Payroll Version

To check your Windward Payroll program version sign into the software after applying the update.

You may be prompted to Update Payroll System Data when signing into Windward Payroll.

  1. Click the Start Update button to complete the upgrade
  2. Click the OK button once the upgrade has been completed.

  3. After signing into Windward Payroll click on the “System Settings” button and choose “About Payroll”.
  4. The system will display Payroll Program Version Payroll SYS Version or greater with a Tax Version of 2022 in the year.

Windward Payroll 2022 Updates are available starting from program versions: (Release) and (Beta). (latest Release Payroll program version) is now available for download as of January 5, 2022.