This chapter interrogates how shifts in the mobility and containment of Aboriginal populations at the turn of the twentieth century, are imprinted on present-day regimes of carceral control. Focusing on mobility and containment through a case study of the relationship between railways and incarceration, in the contexts of colonial and contemporary Australia, this chapter follows the advice of Patrick Wolfe that we should ‘look twice’ – at the other side – of anything taking place at the turn of the twentieth century, a time when ‘the whole world was beginning to shift’, the ‘age of capitalist imperialism was dawning’ and the ‘horseless carriage’ was coming (Wolfe, 1999: 41). Tracing the movement of certain ideas that have confined Aboriginal people in Australia, from the beginnings of the railways to the present, in what follows, the chapter articulates how such ‘conceptual imprisonment’ continues to enable colonial systems to profit from Aboriginal people, including imprisoned Aboriginal labour, in the interest of and for the benefit of a more mobile white population.