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For the new group-based license management, does anyone know if it accounts for similar/overlapping licenses?
Like if I have a group called E3 users and group called E5 users, and put the same user in both groups
Will the user get both an E5 and an E3, or will E5 trump E3?
It depends. The service is smart enough to detect "conflicting" service plans (https://docs.microsoft.com/en-us/azure/active-directory/active-directory-licensing-group-problem-res...), but multiple license of the same type can also overlap, accumulating all the enabled service plans (https://docs.microsoft.com/en-us/azure/active-directory/active-directory-licensing-group-advanced)