This essay focuses on epiphanies -- moments when an insight or revelation captures our attention and summons us to become a better version of ourselves. The role of epiphanies in moral transformation, however, raises a potentially troublesome question. Namely, is the cultivation of epiphanies yet another vexed attempt at moral education? Kevin Gary and Drew Chambers do not think so. Here, they make a case for the cultivation of epiphany as a method for promoting moral insight that avoids the twin sins of provincialism and indoctrination. In making this case, they come to an understanding of what a moral epiphany precisely is by drawing on the work of James Joyce and on recent scholarship that addresses epiphanies and education. After setting the stage, Gary and Chambers turn to an unlikely partnership of Søren Kierkegaard and Paulo Freire. Both thinkers have an interest in transformative education, and both share concerns about pedagogies that compromise human agency. In Kierkegaard, Gary and Chambers find the concept of ethical communication, which enables a learner to self-actualize vis-à-vis the help of another. In Freire, they find a pedagogy that is manifestly nonoppressive and yet takes root in moral awakening. As such, they argue that while no teacher can guarantee a moral epiphany, the attempt to cultivate this experience is both worthwhile and ethically permissible.