This article examines the challenges of parent-teacher relationships in an affluent school district, drawing on 30 in-depth interviews of mothers and elementary school teachers in the USA. Professional women who have put their careers on hold to care for their children are apt to define being a good mother in terms of the academic achievement of their children. This results in extreme amounts of involvement and advocacy in their child's education, even when such actions have questionable effects on the larger school population. Enhancement of "good mothering" was found to be done at the expense of teacher professionalism. A small number of entitled-minded mothers were able to make a large impact not only on teacher job satisfaction but on the climate of the entire school due to their extensive networks, levels of advocacy, and critical examination of school processes.