The error see you above is a clear indication that "Windward POS Device Manager" has failed to register in Windows. Causing it to fail to start.

Windward POS Device Manager is a small application that comes with the software that handles some of the POS devices like (Pole / Customer Display, Cash Drawer, etc). So this is an important application for front tills or cash registers. Not so much for back-office computers but fixing it is really simple.

There are 2 ways you can do this.

Method 1 - SystemFive Argument

  • Right-click on the System5 shortcut on the desktop
  • On the TARGET: field, go to the very end of it, create 1 space then /regserver
  • Click on APPLY button, then OK
  • Now run System5 as an administrator and login

System5 should not load or open, if it does then this did not work. What it does is simply register System5 in the windows registry. Then you can take out “/regserver” from the shortcut and run System5 normally.

Method 2 - Toggle WindwardPOS.exe application to run as an administrator for all users

  • Right-click on the System5 shortcut on the desktop
  • Select “Open file location”. This will take you straight to the directory of System5 installation files
  • Locate “WindwardPOS.exe, right-click on it and select PROPERTIES
  • Switch to the COMPATIBILITY tab

  • Click the “Change setting for all users” button at the very bottom
  • You will then get a 2nd window where you can enable “Run this program as an administrator”
  • Click APPLY, OK & OK to close all windows and log in to System5


You will still get the error pop here but that's OK, we are expecting that. Just click on the “YES” button and log out of System5. 

  • Now go back to the System5 installation directory
  • Right-click on WindwardPOS.exe
  • Change setting for all users button
  • Uncheck “Run this program as an administrator
  • Click APPLY, OK & OK to close all window
  • Log back into System5 normally and the error should be fixed