This book looks at the way the 2020 Second Nagorno Karabakh War allowed urban spectacular transformation in war actors’ attitudes towards space and transnationalism. It concentrates on some specific events, including pre- and wartime life in the Nagorno Karabakh political capital Stepanakert and compelling historical and cultural heritage issues in the cultural capital Shushi and its meaning for the Armenian population worldwide. Attention is placed both on wartime social and urban changes and to the destruction, or attempted destruction, of Armenians cultural heritage during the conflict and in post-war Azerbaijani occupation. The first part of the book reconstructs the historic and religious context of Nagorno Karabakh, linking it with the regional geo-political dimension; meanwhile, the case studies analysed in the second part of the book will help understand spatial meanings (e.g., towns, cultural centres, monasteries) and the symbolic value of urban heritage while also discussing some conflict markers in the context of theories of transnationalism and diaspora studies.