The purpose of this study was to explore the range of perceptions of student affairs practitioners regarding student affairs assessment practice. This was accomplished by integrating various individual and environmental factors into a comprehensive framework that encompasses the multiple levels of the social ecological model (McLeroy, Steckler, Bibeau, & Glanz, 1988). Further, the study was intended to investigate whether background characteristics, such as education level, position and area in student affairs, or the assumptions individuals hold about the role of student affairs, are associated with differing viewpoints. This investigation was expected to help bridge the critical disconnection between the espoused value of assessment in student affairs and the actual integration of assessment into practice. This study employed the methods and techniques of Q methodology to illustrate the subjective viewpoints of 44 student affairs practitioners regarding assessment of student learning in student affairs. Participants from various functional areas, position levels, and institution types shared their views regarding assessment in student affairs by rank ordering assessment-related statements into a forced distribution ranging from “most like my beliefs” to “most unlike my beliefs,” according to their beliefs about those statements. Participant sorting data was subjected to factor analysis using a combination of principal components analysis extraction with varimax rotation, resulting in identification of a three-factor solution. Additional qualitative data was collected via post-sort questions and follow-up interviews to assist with interpretation of three participant viewpoints: Assessment-as-Significant, Assessment-as-Irrelevant, and Assessment-in-Isolation. Differences were noted regarding the roles that various, interrelated individual and environmental factors played in shaping practitioner viewpoints of assessment in student affairs. An examination of the data also revealed background characteristics associated with differences among the viewpoints. The emergent results of this study inform the literature on the application of the social ecological model to social science phenomena outside of the public health field, as well as provide practical insight into ways to address the gap between the espoused value of assessment in student affairs and the actual integration of assessment into practice. Implications for future research were also discussed.