Theological translation, a subfield of religious translation, is often overlooked compared to areas like biblical and liturgical translation. It shares similarities with scientific and technical translation, particularly in its focus on precise terminology. This paper explores the translation challenges of key terms from Peter Canisius’ Little Catechism (1558), comparing the 1585 Middle Ukrainian and 1633 English versions. The study has two main aims: (1) to examine how terms representing a community’s cultural experience, like ‘sin’, navigate intercultural communication and (2) to assess the translation of political and institutional connotations in religious discourse, particularly terms related to the Church. The historical and etymological analysis helps us to understand the dynamic nature of language and concepts. It is accompanied by the methods of close reading, cultural axiology, ideological matrices, and associative horizons.