Issue with Security Filtering in a GPO

I am  created GPO's for printer deployments, initially in testing i just added test users to the Security Filtering in the GPO to make sure the correct printers were deploying and they were. when I add a AD security group with the correct users no printers are deployed, gpresult does not show the GPO as applied, Gpresult does show it for users in the filtering group just not the AD security group. I would prefer not to have to edit the GPO to add and remove users from deployed printers