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When exactly does the 90 minute (+ 30 minute random offset) Group Policy update interval begin?

Is it when a PC boots into Windows?

Also, is the 30-minute randomization offset applied each time Group Policy updates, or just once (at the beginning)?

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2 Answers

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It is scheduled after the computer starts, and after group policy is first applied. You can observe this from the 5315 event in the GroupPolicy-Operational event log:

Next policy processing for DOMAIN\COMPUTERNAME$ will be attempted in 112 minutes.  

It will also occur in response to specific events. An example is a network state change. It is not uncommon to observe this during startup, and will be recorded as a 4002 event in the GroupPolicy-Operational event log:

Starting policy processing due to network state change for computer DOMAIN\COMPUTERNAME$ . 
Activity id: {0a3dd15b-b6c6-4ad9-9509-e5d36caf26fa}

The random value is applied each time.

Troubleshooting Group Policy Using Event Logs
http://technet.microsoft.com/en-us/library/cc749336%28v=ws.10%29.aspx

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Yes, the update is applied on the OS loading and logon, and the offset updates are applied after that.

The randomization is applied on each GP update, and is intended to prevent congestion and other complications from lots of clients updating GP at once.

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