Rooted in a history that dates back 1500 years, the concentration of economic activity and infrastructure in Colombo represents an extreme case of urban primacy within the national context of Sri Lanka. Located on the West Coast of the country, the Colombo metropolitan area accommodates a quarter of the country’s 18.6 million population, and is the economic and political core of the country. However, Colombo is a city of extremes. Its modern and well-serviced core stands in stark contrast to the circumstances of more than half of its population, who live in poorly serviced shack and shanty settlements. The proportion of the population living in these areas continues to expand, notwithstanding a history of innovative and participatory approaches to development planning and management. Complicating these development challenges, the potential of the city is undermined by a civil war that has been under way since the early 1980s, taking an immense toll in loss of life, political polarization, and economic opportunity costs. This paper traces Colombo’s historical development, provides a description of contemporary characteristics and challenges faced by the city, and examines the evolution of plans and programmes designed to improve the conditions of low-income settlements in the city.