Singapore’s post-independence leaders perceived the country’s vulnerability in terms of its miniscule size, lack of resources and hinterland, fragile ethnic harmony and geo-strategic location surrounded by larger, and potentially hostile, neighbours. Given such odds, Singapore sought to become a global city by tapping into international flows of goods and trade. Becoming a core node in the global economy also enhanced Singapore’s strategic relevance, upping major powers’ interest in its survival. However, due to its global connectivity Singapore’s exposure to rapidly spreading global risks, such as pandemics and financial crises, has become increasingly noticeable. This paper seeks to uncover a paradox in Singapore’s ambition to become a global city as new vulnerabilities emerge from its highly globalized status. Through a discourse analysis of policy-makers’ statements and speeches, it reveals that a recurrent theme of perceived vulnerability today relates to the extensive global maritime, aviation and financial flows on which Singapore’s continued prosperity depends. The paper concludes that the critical infrastructure that underpin its global connectivity — its airport, maritime port hub and financial centre — can also unwittingly circulate and import global risks such as pandemics, Weapons of Mass Destruction proliferation, financial contagion and terrorist financing, adding a new dimension to how its leaders perceive vulnerability.