Windows 2008 startup script will not run

To troubleshoot it, I would reccomend the following:

1. Try running logged in as your self, just to confirm it works.
2. Create a test GPO and setup this script in there. Then move a test system in there. In the GPO enable your script as you were, but also set the logon scripts to be visable and to run syncronous. Secondly, put a pause statement in your script so you can check for errors.
3. If you haven't done so already, also check your app log to see if there's any errors with the install its self.

Group Policy assumes you are in an Active Directory domain environment, in which case Group Policy Objects (GPOs) are centrally managed and assigned to computers. For individual machines, the Local Security Policy can be used to produce similar results to centrally managed GPOs.

Typically in Active Directory, login scripts are assigned to User objects, though you can also do this through Group Policy.

If you're not using Active Directory, or you only want to configure this on a relatively small number of computers, you can certainly do this with PowerShell using the Task Scheduler. With Task Scheduler you can create events to run at startup, session end, or logon.