For many Black boys, poor academic performance and high rates of school discipline are often related to biases in how they are perceived and treated at school. These biases oftentimes misalign with how Black boys view themselves and how family members perceive them at home. Few studies examine how different stakeholders' perceptions of Black boys manifest and shape the middle school experience. The current study employed an embedded case study design, using data from eight semi-structured interviews to explore incongruence among student, teacher, and parent perceptions of two middle school Black boys' academic and social experiences. Findings showed greater congruence between the boys' experiences and their parents' perceptions of them compared to their teachers' perceptions of them. Of note were teachers' inaccurate reports of the boys' career aspirations and academic interests and abilities. Implications of these patterns and their impact on Black boys' experiences in school are discussed.