This chapter explores the landscape of assessment in the college context, with a particular focus on experiential education. people will begin with some operative definitions, and a discussion of some of the common problems and challenges in assessing experiential education. As experiential education on college campuses continues to rise alongside a real need to figure out how to assess the associated learning outcomes, teaching faculty, administrators, and program-level directors must wrestle with the difficulties of assessing out-of-the-classroom learning in real and meaningful ways. The anecdote, the cherry-picked star studentor class experience, and the passionate advocacy of the converted are no longer enough in this brave new world. A pragmatic approach to assessment in experiential education is one where knowledge is situated within a framework for action. In other words, people have to be constantly mindful that assessment is really about individual, programmatic, and institutional improvement.