Researchers have documented that supporting student needs, particularly their social-emotional learning, is critical to their success in the classroom. However, little research has been done to explore how district and school leaders make decisions about allocating resources (funding, personnel, curricula, and infrastructure) to student support services, especially during times of fiscal constraint. This study explores the ways that some of the largest high-needs districts in the United States decide to provide the needed resources to maintain social-emotional learning and other student supports in schools as well as the effects of these policy decisions on resources and schools. It examines district leaders’ rationale and the bounds that shaped these decisions using bounded rationality theory. It focuses on a seven-year period from the 2006–07 school year to the 2013–14 school year, the time period before, during, and after the 2008 Recession. This study employs both quantitative and qualitative methods. Through a series of fixed-effects analyses, the study explores funding trends and the impact of student support services (SSS) funding on student support service staff as well as academic and non-academic outcomes. These analyses were conducted in two phases. First, the study explores the impact of SSS funding on the outcomes across the seven-year study period for the 120 largest districts in the United States as a reference and, then, conducts the same analyses exploring the impact within 48 large, high-needs, districts. Following these analyses, the researcher conducted a series of interviews with district leaders in 5 high-needs districts to learn how they were supporting the needs of their students and what considerations shaped the decisions to allocate resources to these support areas. Like the fixed-effects analyses, the interviews focus on the seven-year study period, though context beyond these years is included. The findings indicate that changes in student support services funding are related to changes in student support services staff and high school completion outcomes. The experiences of high-needs district leaders provide additional insight into the decision-making process around student support services funding and the observed variation. District leaders expressed various levels of challenges stemming from changes in federal, state, and local budget reductions as well as challenges in specific years like those that followed the 2008 Recession. These reductions coupled with other limitations and considerations led to different decisions across and within these districts. The constructs of bounded rationality aided in better understanding these limitations, district decisions, and the consequences for students and schools.