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AD DS - Some User groups not getting access

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I am in the process of tightening up our AD DS and have run into some strange problems. The most common problem is that if I add users to a group, give that group access to a folder, it works for some groups and not others. Meanwhile, if I take those same users that were in the non-functioning group and add them as individual users to the folder it works fine. 

We are running Windows Server 2012 R2


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