This volume comprises essays by Singapore thought-leaders republished from various issues of Commentary, the annual journal of the National University of Singapore Society.In the first section, chapters have been curated to provide historical context and analyses of Singapore's foreign policy. The second section presents views on the orientation, values and interests the new, fourth generation of national leaders might have to adopt as they address the emerging challenges in this policy domain so critical to the city-state's survival.These highly accessible essays provide the general reader valuable grounding and frameworks for thinking about Singapore's approach in navigating through the geopolitical shifts in its Asian neighbourhood.