This paper considers a set of Portuguese state-funded projects for agricultural colonisation using coerced subjects. In the second half of the nineteenth century, mounting urbanisation, joblessness, and deprivation, resulting in depopulated countryside and a fractious urban milieu, drove experts to seek international examples for institutionalisation and rehabilitation through agricultural labour. Placing those classified as ‘criminals’ but also new outlaw categories such as ‘beggars’ and ‘vagrants’, as well as ‘undisciplined’ and ‘unimputable’ minors, at the forefront of colonising initiatives in areas characterised as empty or unproductive gave rhetorical impetus to settlement plans and to claims of territorial sovereignty and self-sufficiency in imperial and metropolitan contexts. The article examines a range of experiments: in Alentejo in southern Portugal, where the youth re-education colony of Vila Fernando was the country's counterpart to the French colonie of Mettray, and in Angola, where penal colonies for exiled convicts supported the effective occupation of the hinterland. We argue that, despite their differences, metropolitan and imperial projects can be addressed using the same analytical framework as they share an allied set of practices, cultures, technologies, and agents, mobilised to achieve common goals: economic exploitation, population and territory management, confinement, discipline, punishment, and re-education.