This chapter deals with Singapore—in substance, likely Israel’s closest counterpart in the continent, and with which relations have been the most enduring. Examining the circumstances that brought Israel and Singapore together since the 1960s, it presents a fascinating comparison between the two countries’ responses to the challenges posed by their respective environments and documents how bilateral relations first burgeoned out of Singapore’s specific need for military assistance and, indeed, the establishment of a sovereign armed force. The chapter likewise charts the fine line Singapore has had to tread with its regional Muslim neighbors to pursue ties with Israel, which in turn has also shaped the diplomatic, if not military or economic, aspects of Singapore’s relations with Israel. In so doing, this chapter demonstrates the strong ties and complementarities that bind both countries, despite obvious differences including their forms of governance, ways of looking at the world, and conflict management styles.