The government of Lesotho plans to implement a levy on tobacco and alcohol products. The proposed measure is similar to levies that have been implemented in Botswana in recent years. A concern is the possibility that Lesotho’s new levy may stimulate a significant increase in bootlegging between Lesotho and South Africa. This chapter investigates the presence and possibility of bootlegging between South Africa and Botswana, and South Africa and Lesotho, by describing the differences in cigarette and alcohol prices between Gaborone, Botswana, and the nearby South African towns of Mafikeng and Zeerust, as well as between Maseru, Lesotho, and nearby Ladybrand, South Africa.