Troubleshooting Windward POS Device Manager Registration Error (Error Accessing the OLE Registry)
The error see you below 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 two methods to fix this error, see below:
Method 1 – Register Windward System Five Using the /regserver Argument
This method forces Windows to re-register Windward System Five and its related components.
Windward System Five Registration Steps
- Right-click the System Five shortcut on the desktop.
- Select Properties.
- In the Target field, go to the very end of the line.
- Add one space, then type:
/regserver - Click Apply, then OK.
- Right-click the System Five shortcut and select Run as administrator.
- Log in to Windward System Five.

Important: System Five should not be open; if it is, this registration did not execute. After registration is complete, remove /regserver from the shortcut and run System Five normally.
Method 2 – Temporarily Run WindwardPOS.exe as Administrator for all Users
Important: This is a temporary fix only. Do not leave WindwardPOS.exe set to “Run this program as an administrator.”
Temporary Administrator Execution Steps
- Right-click the System Five desktop shortcut.
- Select Open file location.
- Find WindwardPOS.exe, right-click it, and choose Properties.
- Open the Compatibility tab.
- Click Change settings for all users.
- Enable: Run this program as an administrator.
- Click Apply, then OK, and OK again (close all windows).
- Then, log in to System Five.
Note: You will still receive the registry error. This is expected. Click Yes, then log out of System Five and follow the below steps to revert back to NORMAL settings (recommended).
Reverting WindwardPOS.exe Back to Normal Settings
WindwardPOS.exe Reset Steps
- Right-click the System Five desktop shortcut.
- Select Open file location.
- Locate WindwardPOS.exe, right-click it, and choose Properties.
- Open the Compatibility tab.
- Click Change settings for all users (at the very bottom).
- Uncheck Run this program as an administrator.
- Click Apply, then OK, and OK again.
- Then, log in to System Five normally.
After these steps, the Windward POS Device Manager should be registered correctly, and the error resolved.


