How schools could play a role in facilitating youngsters’ transition from school to work or from secondary school to post-secondary institution has become an important educational issue. Against this backdrop, this chapter intends to examine the means of two different secondary schools in Hong Kong of providing support for postschool planning and how these two schools and their teachers make use of the funding from the government to strengthen their support for students’ postschool planning. The two schools under review promoted classroom-based career education programmes which operated from S1 to S6. Talks and visits to businesses, companies and local universities were also organised. However, authentic career-related learning was relatively not dominant in these two schools. The implications for promoting school’s support for postschool planning are discussed.