This study traces the welfare regimes of Mauritius and South Africa from the early 20th century focusing on the historical circumstances that gave rise to the dominance of state-funded old-age pensions within their respective welfare frameworks. It highlights intersections between powerful business interests, the state, and social forces that sowed the seeds of social entitlements. Due to different mobilisation efforts of these social actors, both countries have spawned welfare regimes of different persuasions. Mauritius has maintained its long-standing traditions as a social democracy stretching back to the late 1950s, while South Africa continues relentlessly in pursuit of a liberal welfare state, a journey it has treaded since 1928 when the old-age pension laws first came into effect. While unravelling the innermost workings of welfare state development in Mauritius and South Africa, it also probes the present political and economic circumstances that have kept these two welfare regimes resolutely unchanged. Against this backdrop, it draws parallels between current welfare outcomes and those of old as they continue to chart their way into the future.