The article deals with the eschatological ideas of V.S. Solovyov, which are the most important part of his historiosophy. The author notes that in the works of the philosopher, two largely disparate eschatologies stand out in relief. Despite the presence of many high-quality studies devoted to his work, the question of the ideological metamorphosis that caused this remains uncompletely clarified. "A special change in mental mood," in the words of V.S. Solovyov, which happened to him, has become a mystery both for the successors of his work and for modern researchers. In fact, they were faced with a dilemma: either, when comprehending history, to focus on human freedom and develop constructions of a socio-evolutionary type, or to focus on divine necessity, thereby falling under the influence of deterministic mindsets. The purpose of this article is to analyze the eschatological ideas of the Russian thinker and identify differences in the ideas characteristic of him in the early and late periods of his creative activity. To achieve it, the author resorts to comparative analysis, considering two landmark works by V.S. Solovyov: "Readings on God-Manhood", in which the evolutionary eschatology of the thinker was most adequately stated, and "Three Conversations...", which give a visual representation of the change in the thinker's worldview in the direction of transcendent Christian eschatology. As a result of the study, it is concluded that the dilemma posed by V.S. Solovyov requires not a choice between two different statements but their combination, which is what the thinker tried to do in his life of philosophizing. The most accurate way to the "spiritual testament" of V.S. Solovyov was followed by Russian metaphysicians, who further developed the history of philosophy and eschatology of the transcendental type, accepting the concept of Providence without detracting from the significance of the activity of free individuals capable of creativity.