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How can AD Group Membership be Managed?

I'm playing around with group management in Manager and different ways to achieve a similar thing but are running into some troubles. These are my scenarios:

Added AD Group to the IT Shop (service item and onto a shelf)
Requested service item with group
approved service item with group
ran sync
Not added to group

Added AD Group to business role
assigned user to business role
ran sync
not added to group

selected a users AD account in hyperview
assigned AD Group to AD account
ran sync
added to group

It seems I can only directly AD Groups to AD Accounts via Manager while the indirect assignment either through a Business Role or a Service Item doesn't work. Is there some configuration I'm missing here?

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