Windows GPO's work best on New Profiles

After the last 3 hours of reboots and gpupdate in vain, let’s remember the following rule when working with Windows GPO’s.

When you change a GPO that makes changes to user settings like folder redirection. do the following;

1. Delete the profile from which you intend to test from
2. Run "gpupdate /force" from the Client
3. Reboot the Client (logoff should work but just to be sure.)

In my case I was creating a GPO to redirect student profiles to their network drives. I was doing 2 different Redirects in the same GPO, however only 1 of them was applying. This odd behavior with no error in the logs to speak of was what really blinded me to the solution.

Also for a tip, if a GPO needs to be applied to an OU, but needs to affect user settings instead of computer settings. The GPO has to enable User Group Policy loopback processing mode. This will enable it to apply the users settings to a GPO applied to computers.

The settings is under Computer Configuration, Policies, Administrative Templates, System, Group Policy.