This chapter, explores whether Singapore is truly smart-is it enhancing sustainability, resilience, and liveability, rather than simply making its existing systems more efficient-by assessing the initiatives it has adopted in the pursuit of smartness using the Smart Model Assessment Resilient Tool (SMART). SMART is a decision-making model that aims to assess and promote liveability by placing it at the core of smart cities-delivering individual and societal wellbeing, resource security and efficiency, and planetary wellbeing. SMART can therefore be used by city leaders to support decision-making toward truly smart cities. The chapter describes Strand One of SMART: the analysis of documented initiatives filtered through four liveability lenses (societal, environmental, economic, and governance). Initiatives are explored as to whether they deliver direct and indirect impacts in support of actions that aim to deliver liveability, their timescale, and their reach in terms of impact on the local population. In support of this research a high-level analysis shows the number of primary impacts (direct) and secondary impacts (indirect) from Singapore’s smart initiatives, and importantly where an action toward liveability is not impacted at all.