Since the foundation of the Free State in 1922, Ireland has struggled to interpret its post- colonial building stock: a heritage which to many reflects past economic, social and political domination by an external power, namely temporal British rule. As the country laid the foundations for its new independence, the wanton destruction of contested historical fabric – perceived as a symbol of colonial oppression – was tolerated by a complicit public until the gradual erosion of relevant architecture across the Republic was challenged by agencies such as the Irish Georgian Society (founded in the 1960s). While the tide began to turn, it would nonetheless take decades for the conservation movement to gain real momentum and for the architecture of the imperialist period to be understood as part of Ireland’s cultural palimpsest. Drawing on examples from the Irish urban realm, this paper looks through the lens of the first 20 years of this century to examine the ongoing shifts in attitudes to heritage in Ireland and to ask if the revalorisation of historical architecture can continue to heal the scars of a colonial past. As a sense of identity is constructed – underpinned by collective memory and symbolism attached to particular spaces – the paper questions if the passing of time ultimately produces a nostalgic view, rather than an enduring resentment. And has the critical need for sustainable, adaptive re-use of historical fabric superseded the desire to demolish or to deliberately neglect? Beyond the detail of policies and polemics, it is evident that common ground can eventually be found in the reconciliation of different interests and disciplines in the challenge of decolonisation.