This article uses archival documents concerning Herbert Gladstone, first Governor-General of the Union of South Africa from 1910 to 1914, to explore the enactment of iterative power. Iterative power focuses on the inevitable fallibility of individual decision-makers who respond to, and seek to alter, the spatial arrangement of diverse materials and flows. Focusing on Gladstone's interaction with a critical incident in 1914, the article reveals how he imagined altering the country's unique geography but yet how the iterative power he expressed was ultimately incapable of negotiating the dynamics of capitalist accumulation, race, and the imperial project in South Africa.