The listing of the capital of Eritrea Asmara as UNESCO World Heritage Site in 2017 has raised a series of contradictory questions around Italian fascist colonial heritage: is the nomination part of the longer path of Eritrea’s decolonization and reappropriation of its colonial history or does this lead to the celebration of modernist architecture and its entanglements with colonialism and fascism? This essay draws inspiration from the case of Asmara, as a way to stir a debate around the afterlife of colonial fascist architecture, and its critical reuse. By discussing the interrelated concepts of repair, reparations, and prothesis within the debates in heritage studies and to the practices of architectural preservation, this essay claims a space for architectural heritage in the entangled struggles of decolonization and de-fascistization. Moreover, it reads fascism’s architectural heritage—and its histories of dispossession and violence—as part of modernism’s controversial history of segregation that cut across the southern and northern hemispheres. In so doing this essay introduces the concept of de-modernization into the debate around critical architectural preservation as part of a transnational struggle for justice against old and new forms of fascisms and colonialisms.