This exploratory, comparative study focuses on the leadership challenges encountered by American and Swedish school superintendents in communities that experienced an unexpected increase in the number of refugees being placed their towns. We focused the study on two small communities in northern Sweden and two communities in northern Vermont. Our study draws on social ecological systems theory to examine the responses of school superintendents to the arrival of refugee students and the extent to which the local, state/regional, and national contexts in which they worked facilitated or hindered their ability to respond to these needs. The majority of the data collection for this study was done in 2017 and 2018 and included personal interviews, on-site observations, and document analysis. The refugee students' lives in both Sweden and Vermont were characterized by numerous systems and subsystems, and all four superintendents sought to create linkages between and among these systems, believing that the smaller sizes of their districts made this easier to accomplish. They faced many challenges in their efforts to respond to the needs of refugee students, and the alignment or misalignment of policies at the local, state/regional, and national levels played a significant role in enhancing or constraining their success.