In recent times, schools have begun to focus on issues of wellbeing, engaging with ideas from various fields such as positive psychology. It is in this context that there is a growing interest in humility, rather than this interest having emerged from debates in moral philosophy and moral education. However, to the extent that education for wellbeing initiatives might promote humility as a virtue, it is important to address the extent to which it can be considered as good. This paper critically explores the shift of humility from vice to virtue in the west with the advent of Christianity. Drawing on historical, religious, and philosophical sources, the status of humility as a moral good is brought into question. It is argued that humility can only be understood, like other virtues, within historical, political, and social context. Thus, it is in how humility is operationalised in contexts of social relations that we can evaluate its moral worth. As such, we suggest that educators and schools should take account of the contingent nature of humility, its paradoxes and politics, rather than promoting it as an unquestionable good.