Increasingly global features have created new defining descriptions of borders outside the traditional notion of ‘geography’ or ‘natural’ border characteristics. But within the context of these new defining features emerge border problems similar to those experienced by geographically adjacent territories. The fresh concept of a Jamaica – Britain border is defined by differences between the economy of the former as a developing state and that of the latter as a developed state. This defining characteristic fosters the two main border problems, illegal immigration and drug trafficking, via lucrative opportunities for a better life and huge profits from drug sales. As a far more dominant border problem, drug trafficking has connected Jamaica and Britain in a drug producing and consumption web. The problematic nature of this connection has heralded bilateral efforts to curb drug trafficking across the Jamaica – Britain border. The result has been the strengthening of a Jamaica – Britain focus on border problems, particularly on drug trafficking but also on illegal immigration matters in terms of their connection to drug trafficking. This article analyses the basis for a Jamaica – Britain border. Within that context it examines the problems affecting this border. It demonstrates that Jamaican – British agreements have proven beneficial in curbing border problems across the Jamaica – Britain border region.