Institutional withdrawal policies allow students with academic and personal difficulties to avert or minimize damage to the GPA by dropping a course in which they may risk a grade of "D" or "F," or to reduce credit hours to better manage those that remain. Offsetting costs involve lost tuition, delay of progress, and perhaps wasted effort. Yet in the pressures of the moment, how likely are students to weigh competing factors before acting? Do they consider the implications for financial aid, satisfactory academic progress, admission to the major, or timely progress toward a degree? What duties may the institution share with students to promote informed judgments? The authors explore the rewards and risks of dropping a course in view of the literature on the "W." Further, they explicate their own case study of withdrawal behaviors in an introductory course to the Informatics major to address questions raised in light of the growing literature on student retention and persistence. "What ties may exist between dropping a course and dropping out of college?" "How may student success studies guide institutions and faculty to assist students facing 'W' decisions?" "Of what benefit may this kind of intervention be for them?" For example, "How may proactive assistance in the 'W' process encourage students to pursue the competencies of a college degree amid discomfort and frustration likely having both cognitive and affective elements?" "How may students who persist through this challenge be better prepared for the complexities of their lives and work?" (Kuh, Kinzie, Schuh, & Whitt, 2010).