This article analyses the practices of deportation and transportation of colonial subjects from Libya, Italy’s former possession, to the metropole throughout the entire colonial period (1911–1943). For the most part, the other colonial powers did not transport colonial subjects to Europe. Analysing the history of the punitive relocations of Libyans, this article addresses the ways in which the Italian case may be considered peculiar. It highlights the overlapping of the penal system and military practices and emphasizes the difficult dialogue between “centre” and “periphery” concerning security issues inside the colony. Finally, it focuses on the experience of the Libyans in Italy and shows how the presence there of colonial subjects in some respects overturned the “colonial situation”, undermining the relationship of power between Italians and North Africans.