A qualitative three-case study design was used to explore how mentoring could assist community college transfer students in earning a four-year degree and to answer the overarching research question, How does mentoring facilitate academic success among community college students who transfer to four-year institutions? Two public universities in the mid-Atlantic and a private Jesuit university in the Midwest comprised the cases selected for this research. Four units of analysis (sources of evidence) were used for data collection and analysis: ethnographic observations of transfer student orientations at three universities; website content analysis of three universities; 15 face-to-face interviews with transfer students at two universities; and administrators’ surveys from each of the three universities. The research produced five evidence-based recommendations for four-year institutions providing services to community college transfer students. For example, results from student interviews identified a strong consensus that better academic advising at the community college level is needed and that four-year institutions should have a greater role in credit-specific advising in community colleges beginning early in the students’ community college experience. Overall, the case study analysis revealed that mentoring, even when not giving academic support directly, provided important ancillary benefits that support students academically and that transfer students benefit from a multidimensional approach to mentoring that includes both social and academic support.