Using data from a grounded theory study with 59 college students with disabilities, this article documents the complex process of developing self-advocacy during the transition from K--12 to post-secondary school settings. This article draws on rich student narratives to illuminate the nuanced self-advocacy processes that college students with disabilities adopted as they transitioned from extensive K-12 school-based and familial supports to more independent higher education contexts. Our findings point to evolving relationships students had with their parents/caregivers as they transitioned into college. The process of learning to self-advocate was also shaped by bureaucratic collegiate contexts that required students to develop new levels of self-awareness, assertiveness, and understanding of their legal rights regarding access to collegiate accommodations and resources.