The use of torture and indefinite detention without trial has been a longstanding concern internationally. This chapter seeks to understand the impact of indefinite detention without trial. It will do so by analysing the trajectory of state responses to left-wing movements following the political detention of politicians, journalists, social workers, anti-colonial activists, academics and unionists since the Malayan emergency in 1948. My arguments draw from research data generated during fieldwork undertaken for research on detention without trial in Singapore. Research data consists of 135 oral history interviews conducted with victim-survivors, their families and community members, many of whom shared their experiences for the first time. My research constitutes an original analysis of the sociological ‘blind spot’ of punitive practices that have occurred outside traditional criminal justice institutions and seeks to understand the historical practice of detention and its social harms following 146 years of British Colonial administration that allowed repressive laws to be used in post-colonial contexts. Collectively, my research findings indicate that extensive long-term harms stem from subtle modes of pain delivery to overt modes of illiberalism through police use-of-force, torture, indefinite detention, administrative, immigration and other legal measures that justify performative degradation and punishment of devianised citizens.