This article examines the pedagogical dimension of vospitanie, or character formation, in communist and post-communist education. It explores how vospitanie is conceptualized in two teacher-education textbooks—one from each period—in Ukraine, a post-Soviet country. Comparative analysis shows how conceptualizations of vospitanie have evolved over time and across political regimes. Instruction on vospitanie for future teachers has a comprehensive structure based on the two “pillars” of labour and the collective, with an increasing focus on democracy and humanism in the post-communist era. Even though regime change and ideological shifts led to some modifications in the conceptualization of vospitanie, this article recommends a more decentralized approach and practical instructions for teachers to ensure the concept’s relevance in post-Soviet society. It also suggests that educators today could explore—and implement—some of the ideas developed in the Soviet period to improve character education within Ukraine and in other national contexts.