Students who are at high risk of dropping out of high school encounter serious difficulties and challenges in their school-to-work and school-to-school transitions. While acknowledging that the prevention of high school dropout requires a comprehensive and systematic helping approach, this article attempts to take a close look at one of the possibilities, the utilisation of more effective career guidance to help at-risk students stay on course with their educational pursuit and prospective career planning. The article addresses some major risk factors affecting the target group. It then uses career development and counselling theories, especially the social learning approach, to propose career guidance intervention considerations for at-risk students.