First off, Loopback processing has two modes: Merge and Replace. Since this is a screensaver, I'm guessing that you're using Merge.
Normally, lowest GPO wins. If you have a very top level screensaver policy and 25 OU's down there is a different policy, the policy that is 25 OU's down is the applied policy. If the higher level GPO is Enforced, it should win unless you're blocking inheritance at an OU.
On the surface, this sounds like a Security Filtering problem. Screensaver settings are on the User side... they only apply to users. If you apply a User side setting to a computer, it will be processed by any user logging into that computer. Your best bet is to run a gpresult (as the user getting the wrong setting) to see what policy they're getting.


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