When the war hit Kharkiv in 2022, the urban space transformed at a scale impossible for its inhabitants and artistic community to process. As it turns out, the urban space of Kharkiv was difficult to process long before the impact of drones and missiles. Kharkiv has been transforming for centuries, collecting monuments and memories from the ebbs and flows of history. The authors zoom in on three events over the past decade that reflect how different actors used the cityscape of Kharkiv to make sense of and shape their context: Architect and visual artist Vasylysa Shchogoleva explores the urban space of Kharkiv in 2023 as a place of healing and compassion. Cultural anthropologist Viktoriia Grivina takes us back to 2018 when a piece of street art on a wall became the epicenter of a community conflict. Anthropologist Hjordis Clemmensen opens a window to the workshop of a group of architecture students in 2013 who wished to not only influence the space around them but also time itself.