In Hong Kong, students with special educational needs (SEN) are able to access the senior secondary education in the 12-year free education. Teachers teaching students with SEN have to prepare their students with knowledge, skills, and competency for overcoming the challenges of lifelong learning and career planning. It is well noted the post-school transition period signifies the transition to adulthood and independent life. A successful transition may lead to students’ adaptive motivation to continuing higher education or employment opportunities, which contributes to good quality of life. However, for students with SEN, they often need to face more challenges than regular students do. This chapter first discusses the contextual analysis for the education of students with SEN in Hong Kong schools by analyzing the increasing number and complexity of disabilities, concerted effort in school support and pathways of postsecondary education. However, teachers always reported the uncertainties and difficulties in supporting the smooth transition of the SEN graduates. By taking account of the research done by the authors specifically through a series of focus group interviews to a wide range of stakeholders, the chapter identifies variables affecting the post-school transition outcomes of students with SEN in Hong Kong. With reference to the contextual needs, the identified variables inform the policy change in career guidance and support for students with SEN. Implications and recommendations at individual, school, community, and policy levels are discussed. In regard to the development of career guidance and planning in schools, this chapter will finally conclude the intensive support, supporting strategies, and multiple pathways for students with SEN in Hong Kong.