In the server Security setup with the "ArcGIS Server Built-in" Role Store (the third Security model option), you can't use the Windows Active Domain groups, only individual users. So if you want to create a new server Role [group] that consists of 100 or more users, you have to add them all individually, one by one, even though there already maybe a similar group of users created in the company's Active Domain. This needs to be fixed.