Urban principals lead complex schools. Although such schools often serve racially marginalized students from low-income families, they also exist within an environment that negatively stereotypes the students and their parents. Such stereotypes are even often held by school leaders and teachers in these environments. At the same time, there are often school professionals who are highly successful with urban students and who have substantive critiques of negative stereotypes about urban students and their families. In this case, a group of critically oriented urban school teachers come together, raise difficult issues, and thus provide a dilemma for their principal.