The main aim of this paper is to revisit what is meant by development and to ask what sort of diplomacy is required to pursue a development agenda. The development diplomacy is reconceptualised in this argument, drawing upon economist Amartya Sen’s conception of development as the empowering of fundamental freedoms and upon Costas Constantinou and James Der Derian’s understanding of diplomacy as an holistic endeavour embracing state and non-state actors, domestic and foreign, and seeking the mediation of estrangement and the overcoming of alienation. The paper investigates to what extent Constantinou and Der Derian’s concept of sustainable diplomacy can be applied to Sen’s concept of development as freedom. The paper then considers as a case study the development diplomacy of South Africa, which is at a point of transition from a traditional position as a developing country aid recipient to becoming a development ‘donor’ state. The South African Government’s 2011 ‘Diplomacy of Ubuntu’ draft white paper is analysed in terms of how it measures up to the foregoing reconceptualisation of development diplomacy, and challenges for South Africa looking ahead are identified.