Italian decolonization has often been described as precocious, given Italy's loss of effective control over its colonies as a result of military defeat in the Second World War. In Libya, however, the projects of agrarian ‘demographic colonization’ that became a showpiece of fascist colonialism continued until 1960 and created persistent tensions between Italy and the independent Libyan state. This article examines a key aspect of Italy's protracted disengagement from Libya: the extended colonial twilight in which Italian farmers continued to work land under the aegis of the parastatal Italian National Social Security Institute. The analysis demonstrates that the fascist colonial project in Libya aimed to sedentarize not only rebellious Libyan pastoralists but also the restless Italian agrarians who formed the backbone of Italian mass emigration overseas. In placing families in planned rural settlements in Libya, the Institute and Italian state officials struggled to circumscribe the mobilities of these colonists. Even after 1945 and fascism's end, settlers possessed little freedom of movement, as demonstrated by the frequent obstacles to repatriation to Italy. Examining settlers' experiences reveals the complexity of the ‘long decolonization’ of Italian Libya, as well as how mobility became a key site of contest under fascism and beyond.