Though the poverty encountered by many rural youth encompasses numerous developmental challenges and substantially increases the chances for educational problems, the school context is central to promoting and constraining their development. Therefore, the purpose of this study was to investigate the relationship of school characteristics and schooling experiences to the educational achievement and aspirations of youth from high-poverty rural communities. Differences in the relationship of school characteristics and schooling experiences to the educational outcomes of students from high- versus low-poverty rural communities were also examined. Participants included 6,247 high school students from 43 low-poverty and 21 high-poverty rural communities. Approximately 51.7% of participants were female and the sample was racially/ethnically diverse (66.4% White, 9.2% African American, 8.1% Hispanic/Latino(a), 4.4% Native American, and 11.8% Multiracial). After controlling for student and family background, school characteristics (e.g., lower student-teacher ratio) were predictive of achievement for rural youth from high-poverty communities. Schooling experiences (e.g., positive perceptions of their ability, a sense of school valuing and belonging, and preparation for postsecondary education) were predictive of educational achievement and aspirations for rural youth from high- and low-poverty communities. Overall, the study highlights unique ways schools can positively shape the educational outcomes for rural youth despite community poverty.