The article is dedicated to exploring the peculiarities of creating an epistolary portrait of O. Hai-Holovko against the background of the era. The epistolary heritage serves as an inexhaustible source that remains open and requires careful examination to this day. The article notes that over several decades, Hai-Holovkocorresponded with literary scholars, writers, and public fi gures of Ukraine and the Ukrainian diaspora, including P. Mykhailyshyn, V. Matsko, V. Chumachenko, P. Soroka, S. Fostun, V. Chaplenko. The analysis of preserved letters from the writer has allowed us to reconstruct, in chronological sequence, milestones in the artist’s life path: childhood and youth, during which the codes of personal behavior were established; the early period of life and creativity associated with turmoil abroad, the search for a better fate; the era of the Ukrainian Renaissance of the 1920s-30s and its suppression by the Bolshevik regime; Bolshevik imprisonment, Nazi Gestapo, and fi nally, emigration. All his life experiences urged Hai-Holovko to reassess his worldview positions, ideas, perspectives, and to embark on the path of struggle for Ukraine’s national lib-eration. Literary scholars affi rm that epistolary sources attest to the writer’s ceaseless service to Ukrainian culture under challenging circumstances. The article not only traces the creation of an epistolary portrait of O. Hai-Holovko against the background of the era but also focuses on the characteristics of Ukrainian diaspora fi gures with whom he communicated and collaborated, among them renowned Ukrainian poets and writers such as Olzhych, Teliha, Samchuk, Malanyuk, Barka, and others. The documentary testimonies of O. Hai-Holovko regarding his relationship with Ivan Ohienko are particularly valuable; they touch upon the latter years of the metropoli-tan’s life, illustrating his missionary activity and serving as testimony to his selfl essness. The study reveals the specifi cs of creating Hai-Holovko’sepistolary portrait against the background of the eras – the horrifi c mass killings of Ukrainians by mos-cow (the Holodomor of 1932-1933), World War II, and the period of his emigration.