The purpose of this study was to gather information from educators and parents on their perceptions of the effectiveness of Individualized Learning Plans (ILPs) in assisting students with disabilities in gaining the experiences needed to develop college and career readiness skills. Results from focus groups and surveys of 1,117 parents and 484 educators in three states indicated that while a majority of parents and educators felt that transition assistance was helpful for youth without disabilities, less positive perceptions emerged regarding the adequacy of preparation for youth with disabilities and, particularly among educators, regarding the readiness of youth with disabilities to transition into higher education and careers. Based on these findings, implications for strengthening ILP efforts in schools are discussed.