For versions - see:  System Five Update - On Prem installations versions -

PRIOR TO UPDATING: please review the following articles to ensure system requirements and backups are in place


1. Update Training dataset first - this allows you to view the update in a controlled environment. Provides you an opportunity to review your critical processes for any possible changes before introducing them into your live production. This limits possible frustration and confusion within your business.

2. Do not update your Live environment on Fridays or Saturdays. In the unlikely event there is an issue during your update, we want to ensure our resources are at full capacity to assist.

3. Do not update your live during business hours. Once the new version is downloaded, you will need to ensure all users are signed out of System Five in order to apply the update.

Now that you have the recommended system requirements in place, in most cases you would perform the upgrade on the server first, then upgrade the workstations once the upgrade and conversion of the data is complete.

Before performing this upgrade on the server, you must ensure that System Five on all your workstations is able to Synchronize with the file server. This is done from within System Five. If you see Synchronize with File Server in the drop down, then synchronization has not been setup and must be configured before you begin the upgrade.

See: Synchronize Terminal S5 Version with Server - On prem

System Five Update  - for version or higher

If you are running Version or higher, you can now update System Five easily. Select Utilities in the top menu bar > Windward System Five FTP update.


You may receive the following error if:

    1. the installed license file is not up to date. Applying System Five License codes

    2. you maintenance plan has expired - contact your Account Manager

    3. You are running a beta version of System Five - please contact support to update

If your License is up to date, you will see the following screen. Select Next

Run the update executable

Entering an email is optional

Select "Next"

IMPORTANT: Once the update has been downloaded and you are ready to apply the update, you will need to ensure everyone is signed out of System Five. 

You should now see the new version displayed on your Log in screen: