Students who are overage for their grade, generally due to being retained at one or more grade levels in school, are at increased risk for lower educational attainment. In some districts across the United States, as many as 90% of students overage for grade do not complete high school (Bowers, 2010). Educators, researchers, and policy makers may misunderstand factors related to students becoming overage for grade if they only focus on individual student characteristics without considering structural conditions of schools and neighborhoods that may impact student outcomes. Overage students are disproportionately Black and Latine across the United States and often live in racially segregated neighborhoods. A long history of disinvestment resulting in inequitable social and economic conditions, including inequities in access to a range of resources and services, characterize these racially segregated neighborhoods (Metzger et al., 2015). Inequity between and within school districts may reinforce inequitable social and economic conditions as lower-funded districts do not have access to the same resources as school districts with higher levels of funding. The purpose of this study, therefore, was to advance the understanding of the factors related to neighborhood and school structural disinvestment and students’ risk for overage for grade. Additionally, this study addressed high school level characteristics that may promote high school completion for overage students. The aims of this study were threefold. Aim 1 focused on the context of place by examining the distribution of ninth grade Chicago Public School (CPS) overage students across Chicago neighborhoods, and indicated the extent to which noneducational structures of opportunity and disinvestment (e.g., affordable housing, home ownership, access to green space, and food security) were related to risk of grade retention. Given that inequity among school districts may reinforce macro conditions, Aim 2 focused on elementary school-level characteristics (e.g., school poverty and school discipline) as they related to students who are overage for grade. Furthermore, schools as political, cultural, and ideologically reproductive spaces of¬ten serve as sites of resistance and can support Black and Latine students who are impacted by educational inequity. Aim 3 emphasized how and which schools resisted the effects of inequitable structures by advancing racial equity school climate and cultivating students’ civic and political knowledge to support students who begin high school as overage and promote high school completion. The findings from this study suggested housing affordability, home ownership, school discipline rate, and school poverty rate were most strongly and persistently significant despite accounting for education related factors at the individual level, which means they were most directly tied to the probability of ending elementary school overage for grade. Furthermore, racial equity school climate was associated with stronger high school graduation rates for all students and found to be especially important for students who are overage.