During the fall 2011 semester, 1,089 students dropped an online course at Wilmington University. This loss totaled 11.8% of the initial online enrollment for the fall semester. This number is in staggering contrast to the drop rate for an on-campus course at the university: 6.6%. This chapter uses Wilmington University as a case study to explore why this problem exists and how to solve it: using student survey and administrative data to look at student expectations and satisfaction with current academic and co-curricular services; technical and service needs associated with online learning factors that facilitate course completion and recommend interventions to help keep students on track to complete courses.