This article contributes to the expanding body of scholarship investigating the problematic correlations between racism, the legacy of colonialism, and configurations of national and cultural identity in post-war Italy. It does so through a yet unexplored perspective: that of the attitude of Italian publishing towards literature from former colonies. More specifically, it examines the reception of anglophone Caribbean novels written by ‘Windrush writers’ in the 1950s and 1960s. The article provides evidence of how Italian agents and publishers – belonging to the country’s intellectual elite, and many of whom publicly espoused anticolonial positions – not only proved to be more interested in the exotic, picturesque contents of Caribbean literature than in its historical, ideological, and political significance, but sometimes actively opposed the circulation of texts containing anticolonial or pro-Black identity claims. Some of their comments demonstrate the persistence of racist and derogatory assumptions of an imagined black and colonial Other, and a negation of their identity as both political subjects and cultural producers, if they failed to conform to dominant expectations. The expectations and the evaluation criteria active in the reception of Caribbean novels allow for an assessment of the ambiguous attitude of Italian publishing agents towards colonialism, race, and alterity.