The achievement gap for racially and ethnically diverse students and students with disabilities remains among the most “wicked” problems in education. Data from the most recent National Assessment of Educational Performance (NAEP. NAEP Data Explorer. https://www.nationsreportcard.gov/ndecore/xplore/NDE, 2022) present a stark realization that there has been little change in the achievement gap between White and Black and Hispanic students since the 1990s. Data from the Early Childhood Longitudinal Study—Birth Cohort (ECLS-B), the Early Childhood Longitudinal Study—Kindergarten Cohort 1998 (ECLS-K), the Study of Early Child Care and Youth Development (SECCYD), and National Longitudinal Study of Youth 79—Child and Young Adult Cohort (CNLSY)—reported similar findings, particularly for White and Black students. In this chapter, we advance empirical evidence of disproportionate academic achievement through an in-depth analysis of the 2017–2018 civil rights collection data (CRDC). Analysis of the CRDC data updates current understandings about disproportionality of advanced placement (AP) course enrollment by race/ethnicity, disability status, and gender and, as an indicator of achievement, provides insights about disproportionality in academic achievement. Overall, the risk ratios for all subgroup comparisons were statistically significant, suggesting that the proportion of students enrolled in AP courses by subgroup is not equal. Specifically, Black and Hispanic students remain significantly less likely to be enrolled in these courses, while enrollment is almost non-existent for students with disabilities receiving special education services.