According to the National Center for Education Statistics (2022a), 2.7 million students with disabilities enroll in college each year. Many students report feeling unprepared for the transition from high school to postsecondary education, particularly because of underdeveloped self-advocacy and college-readiness skills (Morningstar et al., 2017). This quantitative study explored the self-advocacy skills of college students with disabilities at a private Catholic university in the Midwest. Two research questions guided the study: (1) What are students’ perceptions of their preparedness for the transition from high school to college? (2) What are students’ perceptions of their current self-advocacy skills in college? The researcher distributed an online survey to 190 students registered with the Disability Resource Office; 19 responded (10% response rate). Results indicated that most students were not active participants in their high school Individualized Education Program (IEP) or transition planning meetings, hindering the development of self-advocacy. While many students could define self-advocacy and identify personal strengths, they also reported gaps in confidence and knowledge of their rights. The findings highlight the importance of structured transition planning, student involvement in IEP meetings, and explicit self-advocacy instruction beginning before postsecondary transition. The study’s small sample size and reliance on self-reported data from students registered with the Disability Resource Office limit the extent to which the findings can be generalized. However, the study provides exploratory insights into the relationship between transition-planning experiences and the development of self-advocacy skills among college students with disabilities.