Evelyn Underhill (1875-1941) was an English Anglo-Catholic writer and scholar of mysticism whose 1922 edition of The Cloud of Unknowing revived modern interest in the text. Her scholarly introduction provides the historical, theological, and literary context necessary for a contemporary audience to understand the medieval work. She places the anonymous author within the tradition of Christian Neoplatonism, tracing his primary intellectual lineage to Dionysius the Areopagite and his psychological framework to Richard of St. Victor.

Underhill’s introduction also frames the text’s esoteric character for readers unfamiliar with contemplative literature. She praises the author’s ability to combine “high spiritual gifts with a vivid sense of humour, keen powers of observation, a robust common-sense” (2), arguing that these qualities prevent the work from collapsing into abstraction or piety. By explaining the author’s key sources and clarifying his warnings against distraction and spiritual pride, Underhill supplies the contextual scaffolding that allows a modern reader to follow the text’s argument. Her work thus serves as an essential bridge, making the anonymous author’s dense and historically distant guidance accessible.

Dionysius the Areopagite is the pseudonym of a Christian theologian and philosopher writing in the late 5th to early 6th century, whose work provides the primary theological source for The Cloud of Unknowing. His treatise Mystica Theologia introduced a formal apophatic (or negative) theology into Western Christianity. This tradition holds that God is so transcendent that no affirmative intellectual concept can grasp Him. As such, one can only approach God by negating all that can be known or said about Him. The anonymous author of The Cloud of Unknowing was a key figure in bringing this tradition to an English-speaking audience, likely having translated Dionysius’s work himself.

The book’s central metaphor of the cloud descends directly from Dionysius’s concept of Divine Darkness. For Dionysius, the soul enters the divine presence by embracing a spiritual darkness where all rational understanding ceases, rather than entering through intellectual light. The author of The Cloud of Unknowing builds his entire practical method on this theological foundation, transforming Dionysius’s abstract concept into the tangible, experiential “cloud of unknowing” that a contemplative must enter through love rather than thought (19).

Richard of St. Victor was a 12th-century Scottish mystic and theologian whose influence on The Cloud of Unknowing is second only to that of Dionysius. While Dionysius provides the book’s abstract theology, Richard provides its psychological framework, explaining how the soul must prepare itself for the contemplative state. The author of The Cloud of Unknowing drew heavily on Richard’s work, particularly his treatise on the soul’s preparation for contemplation, Benjamin Minor.

Richard’s most significant contribution to the text concerns humility. Following Richard, the author veers away from defining true humility as self-deprecation, instead defining it as honest self-knowledge: “a true knowing and a feeling of a man’s self as he is” (34). This clear-eyed self-assessment is the essential first step in the spiritual journey, purging the soul of pride and making it receptive to grace. Richard thus supplies the practical and psychological groundwork for the mystical ascent, providing a structure that prevents the contemplative path from becoming an exercise in spiritual arrogance and instead frames it as a transformative process rooted in virtue.