School district–university research collaborations represent one strategy to increase educators’ ability to use current, research-based information in program decision making and efforts to improve student achievement. However, differences in organizational structures, goals, values, and prior collaborative experiences have made successful school–university research partnerships challenging. This project intentionally structured and examined a mutually beneficial research collaboration between one small urban university with a significant percentage of first-generation college-going students and two local school districts (P-12) to examine high school math achievement and subsequent college math success. One partnership successfully conducted the study and identified actions to increase student success. The other was successful only to the point of partial data collection. This article describes the structures, mechanisms, and conditions that led to the successful partnership and compares them with the unsuccessful one. It contributes to our understanding of developing effective, mutually beneficial school–university research collaborations to improve student outcomes.