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In the transition from economic imperatives to holistic drivers, there has been a gradual move over five policy phases (from 1965 to 2022 and beyond) toward curriculum and school diversification to cater to different students, with more autonomy given to schools to innovate their pedagogy and improve instructional quality to meet their students’ unique needs. Importantly, there has been a shift in policy rhetoric from focusing on educational structures to focusing on pedagogy and instructional quality. To shift pedagogy from being mainly didactic in nature—with emphasis on preparing students for national examination—the Singapore government recognized the need to focus on school leaders’ and teachers’ capacity building to enable new curricula and teaching practices. The school cluster structure was initiated in 1997 to enable collaboration and learning among school leaders, key personnel, and teachers. Opportunities for collaborative teacher learning are provided at different ecological levels: professional learning communities (PLCs) within schools and networked learning communities (NLCs) across schools. Beyond the education system, the Singapore government works with other ministries and community organizations, such as ethnic self-help organizations, to tackle educational equity issues. Ultimately, even though the official policy narrative post-1997 has been a de-emphasis on examination results and educational infrastructure to help improve the instructional quality in schools toward holistic outcomes and improved student well-being have been developed, education systems building co-exists with an alternative underlying shadow education system valued by parents who continue to chase narrow academic outcomes. Tuition and enrichment centers in Singapore constitute the shadow education system.