The delivery of houses for homeownership to low-income urban dwellers has been a cornerstone of post-apartheid policies fighting both land and socioeconomic inequalities in South Africa. In this context, policy stakeholders and scholars have been puzzled by housing beneficiaries who leave their state houses, either selling or letting them. On the one hand, this might signal upward mobility where “leavers” successfully integrate into the housing market, climbing the next rung of the “property ladder”. On the other, it could indicate that “leavers” cannot afford to stay in their state houses and are consequently displaced to worse living conditions. However, due to methodological challenges, research on the experiences and perspectives of “leavers” is scarce. Based on narrative interviews with “leavers”, this article questions the progress/failure dichotomy. Instead, it argues that “leaving” could be construed as people-led reconfigurations of pro-poor housing policy – representing alternative, individually adapted but partly constrained pathways towards inclusion, 25 years after the end of apartheid.