This study examines the impact of digitalization on Ukraine’s tax administration amid ongoing military conflict. In a time when law faces a crisis of distributive justice, the introduction of digital elements adds complexity to tax management by introducing new variables. Grounded in legal realism and the theory of legal formants, this study explores legal challenges and the added intricacies of digital tax administration. Given Ukraine’s unique situation being aggrieved by continuous military aggression, the study departs from traditional comparative legal studies, but rather seeks to provide understanding of the transformative trends in tax administration and the influence of digital tax transplants in conditions of armed conflict and its implications.