The article offers a re-reading of the role played by Sicily in the Imperial rivalry opposing the Byzantine and Islamic empires in the Central Mediterranean, stressing the island’s specific Imperial dimension. With Justinian’s “Reconquista”, Sicily underwent a thorough ideological, social, economic, and strategic integration into the Byzantine empire, ultimately becoming a uniquely “Imperial” province, a status preserved under Islamic rule. The concept of Imperiality and its evolution between the 7th and the 10th century offers a useful heuristic tool to analyse the ideological, political, and economic importance of Sicily for Constantinople and the role of the island as a source of legitimacy for the Islamic polities in the Central Mediterranean. The reassessment of the archaeological data sheds light on the concrete consequences of this Imperial struggle on the settlement patterns over the same period, with the creation of a specific frontier zone, paving the way to new research into the process of internal territorial diversification of the island.