This qualitative study explored the educational journeys of five postsecondary students with learning disabilities (LD) from the perspective of the students and their families. Using a resilience lens, it examined the challenges that they faced and the capacities and resources that facilitated their resilience and helped them achieve their current level of academic achievement and mental health. A retrospective, multiple case study design was used, and a series of three interviews was conducted with each university student with an LD and their families. The participants identified a number of interactions among the students and their parents, teachers, and peers that helped shape and develop the capacities they needed in order to negotiate for the supports and resources that sustained their well-being. These capacities included an awareness and acceptance of their LD and themselves as learners, the self-advocacy skills they needed in order to seek out and negotiate for the supports and accommodations that would help them succeed, the ability to set lofty yet attainable goals, the perseverance to work toward these goals in spite of setbacks and challenges, and the willingness to use the supports and resources that were available to them.