This article argues for the need to view imprisonment as a transformational experience for anti-colonialists in British Malaya and beyond. Colonial prisons were fertile grounds that led to the shaping and restructuring of anti-colonial sentiments. They were also spaces where new forms of collective action, compromises and adaptations emerged. As will be shown, anti-colonialists' subjectivities and positions shifted from initial feelings of fear and submissiveness upon incarceration to the articulation of collective resistance and the manifestation of attempts to subvert and destabilize the colonial structures that bore down upon them. Such circumstances led to the alteration of the everyday practices not only of the colonized, but also of those in positions of authority.