This paper offers an analysis of how and why magical practices is taught and learnt in the initiatory order A∴A∴, a Golden Dawn-inspired school of ritual magic founded by Aleister Crowley (1875–1947) and George Cecil Jones (1873–1960. Under the motto “the method of science, the aim of religion,” the A∴A∴ was saturated by deliberate educational and scientific measures. As a part of their training, students, including Crowley himself, meticulously documented their progress through reflective journaling, in an empirical trial-and-error approach to magic. This paper examines these accounts, drawing from published texts, diaries, and correspondence, to explore how Crowley and his apprentices engaged in daily magical practices such as meditation, rituals, divination, and astral travel to achieve spiritual insight. The analysis highlights the iterative process of learning within the A∴A∴, characterized by periods of setbacks and successes, problem-solving, and rigorous examinations that determined eligibility for advancement to higher degrees. The rich detail in these narratives provides a unique lens through which to view initiation as lived religion. Drawing on social learning theory, this paper outlines an educational theory of initiation, where the situated, participatory, and relational skills spiritual attainment is brought to the fore. It also considers how the A∴A∴ system, as a religious and spiritual institution, engaged with and responded to the cultural and societal dynamics of its time, including the intersections with secular educational and scientific ideas.