When you are trying to determine why policy is not being applied as expected, one of first things you should do is examine the Resultant Set of Policy (RSoP) for the user and computer experiencing problems with policy settings. Using the Gpresult command-line utility, you can view RSoP.

Gpresult provides details on the following:

* Special settings applied for folder redirection, software installation, disk quota, IPSec, and scripts
* The last time Group Policy was applied
* The domain controller from which policy was applied and the security group memberships for the computer and user
* The complete list of GPOs that were applied as well as the complete list of GPOs that were not applied because of filters.

Useful read at TechNet.