Black youth are disproportionately represented in the juvenile justice system as well as school discipline. Many studies have discussed the comorbidity of risk factors, such as academic failure, mental, emotional, and behavioral health problems, low self-regulation skills, special education, etc. as mechanisms by which Black youth get fast-tracked on to the school-to-prison pipeline (Yoon et al., 2019). Synthesizing the literature, in this chapter, we re-conceptualize the role of special education for Black probation youth. We provide some empirical findings as well as critical race theory to highlight the importance of asking research questions separately for Black youth, not simply in comparison to White/European American youth. We also use intersectionality to suggest that the experiences of Black girls must be examined separately from Black boys. We discuss possible factors for continued justice involvement as well as insights into service and treatment planning for Black/African American youth serving probation in the community, especially for those who have needs for special education.