In brief, the five phases of educational policy reforms have seen gradual systemic shifts in four key aspects: (a) from top-down government control toward more bottom-up initiatives and increasing school autonomy for curriculum, pedagogy, and assessment; (b) from centralized direction to increasingly ecological whole-of-system innovations; (c) from teacher-proof instructional strategies to increasingly learner-centric pedagogies; and (d) from creating school access to focusing on instructional quality. Policies are layered upon one another to move the system in these desired directions. In the latest phase, “Learn for Life” (2020 onwards), the shift away from an overemphasis on academic achievement continues, with emphasis on preparing Singapore students to connect, collaborate, create and to be resilient to changing circumstances. This case study is a companion to “Transforming education for holistic student development: Learning from education system (re)building around the world” (Datnow et al., 2022), a summary report that explores the work of building and rebuilding education systems to support holistic student development in six education systems in Singapore, Ireland, Chile, Canada, India, and the United States and in one cross-national system (the International Baccalaureate).