Much of the existing historical record concerning Oluwale’s life in Britain is a product of his encounters with the carceral state. While there is much to be said about what his case reveals about the history of racialized state violence in Britain, this paper specifically focuses on Oluwale’s first points of contact with the carceral state in Britain—during his arrival from Lagos in Hull as a stowaway. Despite having rights to migrate as a British Commonwealth citizen, the manner in which he entered resulted in him spending the first twenty-eight days of his life in Britain in prison. This paper will use Oluwale’s journey to British shores to explore some of the particular anxieties that West African, Caribbean, and to a lesser extent South Asian, stowaways created for border control officials in the years preceding the passage of the first wave of Commonwealth migration restrictions. In addition to examining some of the carceral powers of the immigration officials, it aims to highlight some of the ways that intergovernmental debates about the problem of stowaways anticipated the architecture of seemingly race-neutral immigration policies that would undo the rights of British citizens and disparately impact the flow of what was a largely non-white Commonwealth migration.