Even before COVID-19, university inductees were vulnerable to transitional stressors, which impact upon their psychological well-being and ability to complete their studies. Resilience, as a psychological construct, may be analogous to holding the functioning that supports higher-level academic performance in twenty-first century higher education (HE). Given the significant investment HE requires, coupled with students’ capacity to develop their resilience, universities may be expected to promote psychological resilience in new students. Linking HE to resilience, outdoor adventure (OA) residential programmes have enabled inductees to build components of resilience (i.e., increased self-perception, feelings of control, and intrapersonal relationships) that may heighten their immediate and longer-term academic performance. Yet, few studies have examined the sustainability of these effects. Across five annual cohorts, the self-perceived resilience of 2500 inductees was profiled across three time-point trajectories: (i) pre-OA programme, (ii) post-OA programme, and (iii) three months post-OA programme. Further, the functionality of inductees’ enduring resilience was evaluated for predicting their prospective academic performance at the end of their first year of study. Students’ self-perceived resilience, well-being, and positive recollection of OA experiences reflected their bounce-back ability and a healthy trajectory of productive functioning. Students reporting higher levels of resilience after three months of following the programme were more likely to achieve better prospective academic outcomes. The large sample size ensured that a powerful detection of change was established across time. However, given the absence of a comparison condition across all time points, any lasting improvements in students’ resilience was unable to be attributed to the OA programme. Nonetheless, the results give significant grounds for further research in this direction, including the study of more distinct narrative enquiries at follow-up. In this way, pedagogical practices, supporting effective interventions, may be deployed with incoming students, with the aim of building and maintaining students’ on-going resilience across different learning contexts.