College expansion throughout the twentieth century was accompanied by the growth of a profession centered on supporting student learning and development. Higher Education and Student Affairs (HESA) programs multiplied across the United States to train these professionals with a focus on administration, leadership, and student affairs. As recommended by the Council for the Advancement of Standards in Higher Education and related professional organizations, the more than 280 programs in existence today typically include a course on the history of higher education. For the vast majority of HESA students, this is the only graduate-level history course they will take. For this study, the research team consisted of two faculty members -- one a historian and one a higher education professional -- and two graduate students who collaborated with the intention of deepening student engagement with history through an authentic digital assessment. This article examines the impact of the authentic digital assessment on student engagement, inquiry, research skills, and awareness of audience within the broader context of the history of higher education in the United States.