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This chapter examines the impact of smuggling across the Nigeria–Benin border on Nigeria’s economic development in the post-colonial era. It traces the evolution of the illicit enterprise of smuggling in the borderlands between Nigeria and the Benin Republic to the colonial era, a period when French and British colonial administrators exploited and monopolised trade in their respective colonies (colonial Nigeria and the Benin Republic) to the disadvantage of local traders, a development catalysed people to engage in clandestine trading activities across the respective borders. Furthermore, it establishes that the causes of smuggling at the Nigeria–Benin border during the colonial era varied slightly from those of the post-colonial period. The chapter thus reveals that smuggling along the Nigeria–Benin border shares some characteristics with smuggling in other parts of the world. The economic implications of smuggling on Nigeria’s economic development, the effect of Benin’s economic policies, the geographical terrain of the borderlands as well as the efforts by the two countries to tackle smuggling in the border area are highlighted. Utilising primary and secondary sources, the author recommends that the Nigerian government remain protective, support local industries through adequate funding, adopt proactive legislation to curb smuggling, and improve its border security.