Overview: There has been an increase in the frequency and severity of stress experienced by Canadian post-secondary students, which has adverse implications on their academic success. This work applied the socio-ecological model for health promotion to explore the contextual factors that influence this relationship at the individual, interpersonal, institutional, community, and public policy levels. Methods: Using a qualitative, phenomenological approach, we conducted 38 semi-structured interviews with undergraduate students and on-campus staff who provide services to this population at a post-secondary institution in Southwestern Ontario, Canada. Thematic analysis inductively identified overarching themes among participants’ perspectives. Results: Several positive and negative factors were identified at each socio-ecological model level, demonstrating the complex interplay of demographic, psychological, emotional, social, physical, and academic factors impacting students’ academic stress. Conclusions: A lack of communication and knowledge seems to underlie many factors, highlighting the need to strengthen communication strategies to promote awareness, accessibility, and availability of services and programs on campus. Results also pointed to focusing on proactive, resilience-focused, upstream mental health promotion efforts at post-secondary institutions to reduce stress and improve academic success. This knowledge can help Canadian campuses better address students’ needs.