This study used survey data to examine relations among homework, student well-being, and behavioral engagement in a sample of 4,317 students from 10 high-performing high schools in upper middle class communities. Results indicated that students in these schools average more than 3 hr of homework per night. Students who did more hours of homework experienced greater behavioral engagement in school but also more academic stress, physical health problems, and lack of balance in their lives. To better understand the role homework played as a stressor in students' lives, the authors explored students' qualitative descriptions of their experiences with homework. The discussion addresses how current homework practices in privileged, high-performing schools sustain students' advantage in competitive climates yet hinder learning, full engagement, and well-being.