The article analyzes the relationship between various works of different genres by A.N. Tolstoy, which were created during World War I. These works share a common theme, which includes opinion pieces such as Tragic Spirit and Haters (1914) and From the Diary for 1917 (1917), cycles of sketches on the military theme (Through Volhynia, Through Galicia, In the Caucasus), and the writer’s prose fiction, including stories such as An Ordinary Man (1914), On the Mountain (1915), Under Water (1915), A Passing Man’s Tale (1917). Tolstoy’s stories of this period rely on the material he collected during his trips to the war zone and reflected for the first time in journalism. The assessments made in these stories were not always a return to specific plots and characters. The author’s involvement in the events described was more evident in his prose fiction. His works had a sense of authenticity due to the spirit of the times and the necessary details he included. The article also traces the genesis of the writer’s attitude towards the war, both during 1914–1917 and later in the novel Road to Calvary (1919–1921).