The themes of spiritual ascension and mystical ecstasy in V. Ivanov, which occupy a pivotal place in his literary production, have been recently examined by M. Tsimborska-Leboda in the context of Augustine's theology and by V. Mahlin in the context of Bakhtin's analysis of Dostoevsky's works. The theme of ecstasy has also been considered by Pamela Davidson in her 1989 monograph. The present paper proposes to analyse this very theme, but this time in the context of the theological poetics of Dante's Paradiso. The relevance of this study lies in the fact that, despite a number of immediately discernible parallels, the differences between Dante's and Ivanov's conceptions of ecstasy have not been fully identified yet, notwithstanding the significant influence exerted by Dante’s texts on the conception of ecstasy in Ivanov’s writings on Symbolism. Comparing Ivanov's and Dante's models of ascent, P. Davidson sees a fundamental difference between Ivanov's and Dante's conceptions of ecstasy in Ivanov's rejection of the moral-ethical dimension as a sine qua non of the mystical quest. This article reveals another important difference between Dante's and Ivanov's descriptions of ecstasy, one that concerns the category of “penetration”. Focusing on Ivanov’s articles and Dante’s Paradiso, the article analyses them in relation to the category of “penetration”, to be understood as the ultimate realization of transcendence in Ivanov as well as in Dante’s poem. It highlights the similarity between Ivanov’s and Dante’s thinking as far as the category of “sobornost” is concerned, whereby a vertical relationship with the Supreme Being implies a horizontal relationship with the Other, to the extent of spiritual penetration into the Other. However, it is argued that, while in Ivanov's description of ecstasy the ascent of man and artist begins with erotic rapture and, at its highest stage, implies detachment from all earthly things and separation from them, for Dante the ascent, as described in the Paradiso, is accompanied by spiritual interpenetration which occurs in interpersonal communion even at the height of the mystical vision. The conclusion is that, although Ivanov's other works treat the theme of transcendence in a similar way to how it is treated in Dante, Ivanov’s treatment of ecstasy in his articles on Symbolism differs significantly from its description in the Commedia.