This article uses a micro-historical approach to examine an escape and murder among convict labourers between Cape Town and Stellenbosch in Southern Africa in the 1840s. It does so to demonstrate how imperial mobilities and legal conceptions of property crime were interconnected within settler colonial capital and the intimacies of colonial social worlds. Reforms in penal practice in the British Empire – in this instance, adopted in the Cape Colony from Tasmanian experiments in convict labour and moral improvement – formed part of post-abolition shifts in labour control and the management of the itinerant poor, increasingly guided by anxieties over race. Michael O’Brien, the murderer, was a suspected escaped convict from Australia, who claimed to have survived violent encounters in the Pacific as a missionary. His narrative contrasts with the predominantly regional mobilities and crimes of the other Cape convicts – notably stock theft and petty robbery – that occurred in the contested spaces of law, colonialism and property. This article discusses convict narratives around crime and redemption across a maritime empire, and the affective relations of coercion and care between convicts, overseers, constables and superintendents on the smaller scale of a convict station. It further contends that changes in criminal justice and governance in Southern Africa were thus contingent on the intimacies of scale and affect, on connections between the local, the global and the biographical.