Institutions of higher education are replete with programs designed to position incoming undergraduate students to successfully persist toward a degree and to do and be well along the way. This longitudinal field study of incoming students’ transitional year focused on outcomes associated with two common types of program: bridge programs and living-learning programs. Bridge programs are intended to boost achievement and persistence of structurally disadvantaged (e.g., low-income) students to close the gap between them and their more advantaged peers, usually with some combination of financial and academic support. Living-learning programs are intended to generally promote achievement and persistence through the intentional formation of communities in which groups of students live together in wings of residence halls and engage in curricular and/or cocurricular activities together. Social-psychological interventions have been inspired by critiques that such programs inadequately support students who are at a structural disadvantage. Specifically, critiques have argued that financial and academic support are insufficient, that students also need psychological support. To strongly test that claim, I replicated one of these interventions within a bridge program and examined whether it affected students’ wellness and success at the end of their transitional year, over and above the bridge program itself. I also examined whether living-learning programs contributed to students’ wellness and success over and above living in conventional residence halls, and whether either of those two types of residential groups differed from students living off-campus. Results from the intervention did not fit the theoretical framework on which it was based, the same framework contextualized in the bridge program, or an alternative framework on which other similar interventions are based. Results regarding residential groups suggest that living-learning communities did not augment wellness or success, at least at the particular institution under study. Rather, living on campus generally is associated with a greater sense of social-belonging, higher life satisfaction, more extracurricular activity, and taking advantage of campus resources. Practical advice and recommendations for administrators and researchers are outlined in the Discussion.