This article offers a new approach to the study of Singapore history through an interrogation of the city-state’s borderedness and openness to Malaysian workers during the 1970s and 1980s. This was the period in which the foundations of modern Singapore were laid, as the state opened its borders to meet the demand for labour in the industrialisation program. Yet, this open-border policy was overlaid by a state system of work permits, levies and penalties designed to control migrant labour. The policy turned contradictory over time, attempting to reduce Singapore’s reliance on foreign workers while in practice increasing their numbers. Despite its best efforts, the state was never totally successful in policing the border as workers and employers found ways to circumvent the controls. Regardless, state efforts to adjust border, labour and immigration policies to meet the immediate and imagined contingencies of its modernisation agenda were extensive and relentless. This suggests that we need to consider in more nuanced ways recent notions of borders as zones of transgressiveness that are free from state controls. In the city-state of Singapore during the 1970s and 1980s, the border was a complex zone of both control and transgression.