This paper examines the paradoxical development of Human Security in Singapore. Despite achieving a high level of human security nationwide, the heavy top-down approach has not sufficiently empowered the Singaporean society to independently cope with risks at the community level. The study covers the following areas. First, a brief background on Singapore’s efforts to achieve high levels of human security is presented. Second, we discuss that the downside risks or inadvertent policy implications for human security are the result of uneven access to, or provision of, protection by the state and a lack of empowerment (i.e., actions that enable people to cope with risks). Third, we give a snapshot of the Singapore government’s recent efforts in mitigating the downside risks, particularly after the watershed 2011 general elections. Fourth, the study discusses Singapore’s policies in mitigating transnational human security risks. Given Singapore’s small size and proximity to other states, the city state is aware of its vulnerability and hence needs to take steps to mitigate transnational risks that would have a spillover effect into Singapore.