The official narrative underpinning Eritrea’s nation-building project describes the path toward independence in terms of the struggle against three uninterrupted colonial projects: the Italian, the British and the Ethiopian one. This article aims to provide more complexity to this picture by taking into account the evolution of the Italian foreign policy towards Eritrea in the first years of the Federation with Ethiopia (1952-1962). It looks in particular at the relationship between Rome and two prominent members of the independence bloc: Woldeab Woldemariam and Ibrahim Sultan. Archival sources from the Italian Ministry of Foreign Affairs, Banca d’Italia, Banco di Roma, and the National Archives of the United Kingdom highlight an enduring Italian support to Eritrean opposition groups’ quest for autonomy against Ethiopian domination, though this position will gradually change in the second half of the decade.