This study examined the effects of social influences in the lives of an ethnically diverse sample of fifth through eighth grade students with and without learning disabilities (LD) using survey data and academic achievement scores collected in 19 Chicago public schools from 1993–1997. Similarities and differences in student perceptions of school, family, and peer group contexts were examined. In addition, longitudinal data were analyzed using hierarchical linear modeling (HLM) to identify contextual influences on changes in student reading achievement over time. Comparisons of student responses confirm and extend existing findings in the literature concerning the perceptions of students with LD of their social environments. In particular, having a learning disability was associated with consistent, mostly negative, effects on social relations across the contexts of students’ lives, regardless of gender, race, grade, and socioeconomic status. In addition, student perceptions of their friendship groups were found to have small, but significant, effects on their growth in reading achievement over the course of middle school. While students with and without LD had somewhat different views of their social contexts, the processes working within these environments appeared to affect their reading achievement in similar ways. The results suggest that careful attention should be paid to the social contexts of students’ lives when planning academic interventions.