The policy ‘Administratively assigned offline files’ is not applied when there is only a Computer Configuration policy and no Offline Files settings exists under user policy in Windows 7 or Windows Vista
Consider the following scenario:
You enable the Offline Files feature on a computer that is running Windows Server 2008 R2, Windows 7 or Windows Vista.
The administrator has configured Offline Files using Group Policy (Group Policy Object Editor, Computer Configuration, Administrative Templates, Network, Offline Files: Administratively assigned offline files) in Windows 2003 Active Directory environment.
Note the setting in machine based Group Policy Object
The GPO gets applied to Windows Vista or Windows 7.
Result: The offline setting is not enabled on Windows Vista or Windows 7 systems and no network files and folders are getting pinned.
For more information on this issue, including potential causes, workarounds, and resolutions, see: Microsoft KB Article KB2379156.