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Windows Server 2008 R2.

Can AD be set up so that any user added to a particular OU automatically be assigned to a particular user group?

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There is no functionality to do this natively. You can have something like a PowerShell script called on a regular bases from Task Scheduler though.

You would use the Get-ADUser and Add-GroupMember, both of which are parts of the ActiveDirectory module for PowerShell that is part of RSAT.

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