Hong Kong education is the legacy of the Confucian Chinese culture and British colonialism. While regarded internationally as a hub of world-class education, Hong Kong education is also said to be examination-oriented and results-driven, trading off the psychological health of secondary students, teachers, and parents. We argue that positive education, with adaptations to local context, provides a balanced approach that promotes both well-being and academic excellence. This paper first explores the historical, cultural, and societal factors that have shaped Hong Kong education system. Through which, we identified teacher resistance and reactive parenting strategies as key local challenges to positive education implementation. The second part of the paper discusses the implications and recommendations. The cultivation of teachers’ occupational well-being and the provision of autonomy support from both teachers and parents foster positive relationships with students, which contribute to student well-being and academic diligence. A model is suggested whereby it includes rigorous measurement that are cultural-specific for implementing positive education in Hong Kong.