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The past two decades have witnessed an exponential growth in the use of technology in our daily life. Notwithstanding its phenomenal influence, the use of technology in education remains sporadic and disjointed. The promise that technology will bring deep-seated changes in the way that educators teach and students learn remains, disappointedly, elusive. This paper argues that the lack of systemic frame of reference may have explanatory power over such less than impressive performance of ICT in education. Tracing the trajectory of Singapore’s ICT-related policies in the educational sector, this paper adopts the complexity lens to study the systemic policy changes that are imbued in the different stages of Singapore’s ICT-based reforms. In particular, the paper delves into the three constructs of complexity theory: self-organisation, coevolution and fitness landscape. By juxtaposing the interdependencies of these three concepts against the backdrop of Singapore’s educational landscape, the paper contends that the complexity theory perspective has the potential to help policymakers understand the dynamic and complex nature of reforms so as to devise multi-faceted solutions that will address the concerns of all key stakeholders in the learning ecology. Implications for policymaking are also discussed.