This paper charts the emergence of and the movement towards new thinking on sustainable transport in the City of Cape Town, South Africa, and the adoption of a set of indicators for sustainable transport. The paper centres on two themes. It reviews the sustainable transport concepts debated and later adopted by the City of Cape Town. It then examines the day-to-day practice of developing sustainable transport indicators in Cape Town over a 14-year period, from the advent of democracy in 1994 to the present day, with a particular focus on the 2007 to 2009 period. The paper tries to shed light on the process by which ideas of sustainability get translated into indicators in the midst of many constraints including limited staff resources, uncertain politics, and changing policy priorities.