This basic interpretive qualitative study explores the multiple levels of context in which Higher Education and Student Affairs (HESA) Master's programs exist and how those levels of context influence curriculum development and teaching. Utilizing interviews with 44 HESA faculty members across the United States and Canada, findings illustrate how concrete curricular choices are embedded in and shaped by relationships between institutional, profession, and policy contexts. These levels of context exist within even broader sociocultural and temporal contexts. These findings have implications for how HESA faculty members navigate, the often bureaucratic nature of, curriculum development processes as they train student affairs practitioners for the professional problems of the future.