There is a growing body of research focused on the mathematical experiences of Black males in the United States of America. This research has emerged to challenge the dominant narrative in mathematics education focused on Black males' low performance on international, national, and state standardized tests. There is very little research that has explored the impact of high-stakes testing in mathematics on Black males in urban areas. Using qualitative research methods, this study examines the middle school mathematics experiences of four Black males and provides insight into their responses to challenges they face in urban communities, schools, and math classrooms. Critical race theory was used to illuminate Black males' desire to be challenged in the classroom and describe the community, school, and classroom conditions that impact their lived realities and mathematics experiences.