Outdoor orientation programs have a growing literature demonstrating positive impacts with students transitioning to college (Bell, Gass, Nafizer, & Starbuck, 2014). One of the most valued outcomes for colleges and universities is retention of students until successful graduation. This is an outcome few outdoor orientation researchers have studied, but one that many programs claim to influence. This paper provides an overview of the literature of outdoor orientation programs retention studies, with specific attention placed on selection bias. This study used a control group (randomized selection), a convenience group (nonparticipants), and a comparison group (matched by covariates) to assess the differences in retention outcomes. Findings indicate (a) similarities between sampling through random selection and covariate matching, but not by convenience sampling and (b) generally positive retention results for participation in outdoor orientation programs, including small effect sizes for retention (OR = 1.91-2.38) and graduation (OR = 1.07-1.81), but few statistically significant results (p < 0.05).