The high dropout rate in urban high schools, particularly among poor and racial minority youth, continues to be a vexing problem confronting public education in the U.S. Although much research and many prevention efforts have been devoted to this issue, dropout rates continue to soar. In this article, the authors present a case study analysis of an urban high school that was attempting to address the high dropout rate. Instead of focusing on social and academic risk factors that assume the problem lies in the student and his or her family, we examine how the culture and structure of the high school influenced teachers' instructional practices and resulted in contradictory beliefs about students and their families. These contradictions between school culture and structure, instruction, and many students' home culture contributed to the school's high dropout rate.