Research on informal settlement upgrading tends to focus on one-off case studies. This article investigates the changing experiences, over nearly 25 years, of people living in an upgraded informal settlement. We sought to determine how the perceptions of the residents of Freedom Square changed. Our latest survey (2014) included responses from 199 household representatives and followed earlier surveys. Firstly, we find that the upgrading of Freedom Square represents a first step towards ensuring the housing rights of black people in urban South Africa. Secondly, spatial infilling and locational advantage continue to play valuable roles. Thirdly, dweller control, in terms of which residents themselves are able to design extensions to their houses, remains important. Fourthly, social cohesion among community members is proving to be more important than access to a stand. Fifthly, urban management remains an important long-term requirement. Lastly, elements of informality persist in the area.