The aim of this article is to rethink the way scholarship conceives Gregory of Nyssa’s so-called mystical theology by directing attention to his account of hostile powers in the Homilies on the Song of Songs. In recent decades, debates on “divine darkness” have governed scholarly readings of Christian progress in the homilies. However, through his allegorical commentary, Gregory also provides an extensive account of the history, ontology, and activity of the devil and demons, while also instructing Christians on how to defeat them. According to this account, only Christ is victorious in the proper sense. Therefore, believers must participate in Christ’s victory by journeying the way of the Homilies on the Song of Songs. This begins with baptism and continues with self-knowing, prayer, pure thoughts, and correct worship. Therefore, these homilies—communicating Gregory’s vision of “divine darkness”— also provide an extensive account of how to overcome adversarial powers whose goal is to prevent the bride’s union with God.