This study examined (1) student perceptions of school connectedness across racial subgroups (African American, white, Hispanic, Asian or Pacific Islander, and Other); (2) the relationships between student perceptions of school connectedness and school-level variables of racial composition, teacher racial composition, and socioeconomic status across African American and white racial groups; and (3) the relationships between school connectedness, teacher racial composition, peer support, adult support, teacher support, discrimination, and expectations when examining African American middle school students perceptions, as measured by the Georgia Student Health Survey 2.0. These relationships were explored using data collected from middle school student (N = 308,887) across 580 public schools in Georgia. This three-part, quantitative study employed one-way analysis of variance (ANOVA) and an integrated, multilevel modeling approach (inclusive of confirmatory factor analysis and structural equation modeling) for statistical analyses. The results indicated that perceptions of school connectedness are practically significantly different across racial groups, with the largest difference between white and African American students. Contrary to extant research, African American students were more connected to schools relative to white, Hispanic, and multiracial and less connected than Asian or Pacific Islander racial groups. Gender had a weak association with connectedness across African American and white racial groups. Connections to school decrease as students advance in grades, above and beyond other school- and individual-level factors included in the study. Lastly, the results point to the need for student-driven conceptions of school connectedness. These findings are discussed in terms of the challenges facing racial equity in understanding, contextualizing, and developing culturally sensitive measures of school connectedness. Study limitations, future directions, and implications are discussed.