This chapter deals with smuggling as a historical phenomenon. It begins by addressing the relationship between the definition, demarcation and enforcement of international borders in distinct types of terrain, on the one hand, and the incidence and modes of smuggling on the other. The chapter then turns to a more detailed comparison of instances drawn from across Europe, Africa, South East Asia and North America. These exemplify three different patterns. The first is where smuggling was a response to colonial revenue imperatives, for which colonial West Africa provides clear examples. The second is where the intention was to restrict the flow of commodities, substances and people deemed dangerous. Here the examples are drawn from colonial West Africa (religious tracts and firearms), South East Asia (firearms and narcotics) and the US–Canada border (people and alcohol). The third pattern is where a border suddenly emerged during a moment of political rupture. Here, the primary focus is on the appearance of the border between Northern Ireland and the Irish Free State in 1922. The general lesson is that while smuggling was a response to state practices, the borderlands as lived spaces were themselves shaped by the ideas and daily strategies surrounding smuggling.