Background: Child well-being, which includes physical, mental, and social health, has a critical effect on academic performance. Schools face many challenges in meeting needs for child well-being. Schools in low-resource areas, including the Mississippi Delta, face greater challenges when meeting student needs. Methods: Eleven focus groups with middle school students and 12 interviews with teachers, staff, and administration in one Mississippi Delta middle school were completed in 2019. The Social Ecological Model and Theory of Organizational Readiness for Change were used as a framework for the study. Results: Focus group data with middle school students and interviews with teachers, staff, and administrators show that academic stressors play a major role in student well-being; yet, teachers, staff, and administrators face immense pressure to achieve high test scores. However, students seem to be encouraged by a positive school environment, which could help minimize some stressors. Conclusions: It seems that small improvements to the school environment could have a significant effect on student well-being, especially when school infrastructure and limited resources do not support comprehensive changes.