This study of Basotho attitudes towards and meanings of the Lesotho‐South African border along the Caledon River valley, next to what is historically known as the Conquered Territory in the eastern Free State, details the long history of struggle and co‐operation between the Basotho and the white inhabitants of the Free State. Analysis of the specific nature of the flow of commodities, trade, labour, and contraband over the Caledon River border bridges during the past ninety years demonstrates that the Caledon is a political rather than an organic social boundary, and that the river itself is the centre of a cross‐border way of life, paradoxically both obstructed and united by ‘international’ border stations. The conflictive history of postindependence Lesotho politics reveals how profoundly attitudes towards and relations with South Africa, and specifically the border communities of the Free State, are implicated in every aspect of the country's national existence. The lack of any effective sovereignty for Lesotho has problematic implications for the maintenance of border controls and restrictions on immigration from Lesotho in the post‐apartheid period. In practice the border posts can operate with neither credible efficiency nor neighbourly openness, because the border is not an international political or economic boundary and control point but rather a business. Political integration of Lesotho into South Africa in some form is seen as inevitable, notwithstanding the desire and efforts of either or both the Lesotho and South African governments to prevent it.What ‘the Basotho’ ultimately want, independence or no independence, is the continuing development of the Caledon Valley's organic multi‐racial way of life. SADC's military intervention in 1998 revealed deep fissures in Lesotho society. Ironically, military intervention to stabilize Lesotho's political situation appears to have accelerated the movement towards eventual incorporation.