Problem: 

With Windows Password Sync (WPS) enabled, a user’s Trusted Drive Password is not successfully synced with the users Windows Password.

Solution: 

If the drive is not syncing the Windows Password, it could be due to the GPO not being pushed down successfully. To confirm this, please open the Registry on the client machine, and navigate to HKLM\SOFTWARE\Policies\Wave Systems Corp\Trusted Drive Manager. If you do not see the Trusted Drive Manager folder, or the key for WPS is set to 0, then the GPO has not been successfully pushed down.