The international literature reflects the significance of transition services for postschool outcomes of students with disabilities. In 2008, the Hong Kong Government introduced a policy to support students with disabilities, especially those with specific learning difficulties (SLD), to transition to postschool life in inclusive settings. This article focuses on the status of policy implementation in Hong Kong and its link to the higher education participation of students with SLD. Analyses are based on expectations of policymakers for school practices in transition services, parental experiences, and a discussion forum involving postsecondary students with SLD, advocacy groups, and university student affair personnel. Findings reveal a lack of expectation for implementation and school accountability from policymakers, an extremely low participation rate of students with SLD in higher education, a slow development of support systems in higher education, and the significant role played by an advocacy group on moving the higher education support forward in the absence of a policy mandate. By focusing on the close relationship between transition services and postsecondary outcomes, the use of legislation for disability policies to ensure the provision of transition services and the role of self and external advocacy to lobby for such legislation are recommended and discussed.