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Following a successful counteroffensive that resulted in the liberation of wide swaths of territory in spring and summer of 2022, the Ukrainian state and its population found itself reckoning with another consequence of Russia’s recent war of aggression: how to deal with the thorny issue of wartime collaboration. In addition to extrajudicial efforts to deal with collaborators, the state has updated laws and begun extensive efforts to hold collaborators accountable in court, while communities in the Kharkiv and Kherson regions have begun to reckon with the consequences of wartime choices and actions. Questions about wartime behavior, collaboration, and post-liberation retribution and justice have long and painful legacies in 20 th century Ukraine. This paper explores the relationship between these historical legacies and the present war. Working with extensive on-the-ground reporting from the weeks and months after liberation, the paper examines wartime behavior in light of a broader historical and social scientific literature on collaboration and occupation, highlights salient takeaways how and why Ukrainians made choices under occupation, and asks questions about how historical legacies of collaboration interact with the present. Further, the paper explores related questions to the Ukrainian government’s execution of justice, in particular on the many obstacles to prosecuting collaboration, and again, issues of historical residue and resonance. The paper concludes with suggestions for future avenues of inquiry on this topic and a wider takeaway about the relationship between past and present in contemporary Ukraine.