The transition to university is a significant life event that can be difficult for many youth. Making this transition while managing mental illness is likely to compound these difficulties for both youth, and their parents. This dissertation aimed to explore the experiences of first-year university students who reported a mental illness prior to attending university, as well as the experiences of their caregivers. Study 1 examined how youth perceptions of their relationship with their parents and their own personal strengths related to measures of well-being across a clinical and comparison sample of students. Results suggest that both relationship with parents and youth personal character strengths are important in predicting youth well-being to a similar degree across the clinical and comparison samples. Character strengths were not supported in serving as a moderator between parent relationship and youth well-being. Study 2 focused on a subset of the clinical sample and included information from a parent. This study examined parents’ experience of reward and burden associated with caring for a child with a mental illness, and how this related to parents’ virtues and student functioning. Further, parents’ role in supporting the transition to university was examined qualitatively from the perspective of youth and parents. Parent satisfaction with the parent-child relationship was associated with subjective caregiver burden. Parent virtues were not associated with caregiver reward, burden, or youth functioning in the ways expected, though some relations may be non-linear. Higher reported rewards of caregiving were associated with higher levels of youth reported life satisfaction, while higher levels of burden were related to depressive and anxiety symptoms and lower life satisfaction. Parents and youth described a number of similar themes regarding how parents may best support their youth as they manage university and mental illness. Implications for prevention and intervention efforts for post-secondary institutions are discussed.