This article places the current Libyan conflict in historical perspective by focusing on the dynamics between the country’s two main regions (Tripolitania and Cyrenaica) during key moments of the 20th century. Particular attention is given to the different way each of the two regions approached the early period of Italian colonialism, from 1911 to 1923. The paper shows that historical relations between the two regions are characterized by both independence and interdependence and that this pattern is reemerging as the country transitions to a new era.