Between 1912 and 1940 Italian authorities in the Dodecanese implemented demographic, cultural, and social policies aimed at framing a new imperial space. Colonial practices of violence and repression coexisted with pervasive attempts at cultural and ideological assimilation, with the ultimate goal of creating a new subject identity for the islands’ inhabitants. This paper presents some of the mechanisms of this system from below, using local Italian and non-Italian sources. The explored mechanisms are: the demographic policy implemented during the Greco-Turkish war; the impact of the special Aegean citizenship; and the educational tools specifically tailored for young locals. These practices and the survival strategies implemented by local communities have shaped local memories, which recall Italians in ambivalent terms oscillating from the “Good Italian” image to resentment of the imposition of a quasi-colonial status of subject.