This commentary examines the performance of southern Africa's regional institutions against the backdrop of the changing regional context since the late 1990s. The first section reflects on the relationship between successive geopolitical changes and efforts to keep the Southern African Customs Union, Southern African Development Coordination Conference and Common Market for Eastern and Southern Africa relevant over time, as well as the frequent mismatch between the ambitions for regional integration institutions and the evolving realities. Thereafter, I consider how far the optimism that post-apartheid South Africa would transform itself from regional pariah to leading partner in reaping collective peace dividends has been borne out, using the examples of recent trends in conflict and instability, in nationalism and nation building and in infrastructure and communications. Finally, the fitness of current institutions to address new challenges in the form of global environmental/climate change, the ongoing urbanisation and the increasing engagements by China and India in the region is assessed.