Childhood obesity is a pervasive health issue, with multifaceted implications for developmental trajectory. Participants included 5,573 K-5 students enrolled in a high-poverty urban public-school setting. Through an informal yet holistic assessment process, students identified as exhibiting overweight issues were compared to peers not designated as overweight across several relevant categories. Overweight students were more likely to be from lower socioeconomic backgrounds; have a high association with special education service needs; represent a more intensive overall risk level as perceived by student support staff; and mostly exhibit decreased performance in report card grades, standardized test scores, and academic engagement. Results confirm previously documented disparities in school functioning and consideration for at-risk status; this is especially relevant in an underserved context, in which regular access to services may be limited. Therefore, reliance on initial screening measures becomes necessary as a preventative mechanism to better assist children in need and to facilitate intervention planning.