Work-integrated learning (WIL) is an expanding practice in Canadian non-clinical health-related undergraduate programs. WIL participants frequently encounter failure experiences, yet there is limited literature exploring how students overcome failure and how instructors can support this process. This study aimed to understand how students overcome and learn from failure experiences in a non-clinical undergraduate health-related WIL program. Using a constructivist grounded theory approach, in-depth interviews were conducted with 10 previous students from an established WIL program. Iterative cycles of data analysis and constant comparison generated a theoretical explanation highlighting how students overcome failure by renegotiating their expectations through 1) experiencing and managing the wave of emotion, 2) modifying expectations of self and others, 3) redefining success and moving forward, and 4) building flexibility of expectations. This research presents failure as a tool for learning and a steppingstone toward success. Findings inform a pedagogical framework to optimize student learning from failure.