Surprisingly little research has been published about Chan perspectives on death, and even less is known about how Chan conceptions of death and dying have evolved over time. Sometime during the twelfth century, the Caodong Chan master Weizhao famously admonished his disciples to “be like someone who has died the great death,” alluding to the death of the deluded mind, or enlightenment. In a twist on Zhauangzi’s famous adage, Weizhao tells a student: “Why be concerned about returning to life if one does not yet know how to die? Why be concerned about enlightenment if one does not know how to put out the flames of delusion?” The great matter of death seems to render all other koans irrelevant. At the same time, pre-Buddhist influences and human emotions continue to affect the ways in which Chan practitioners face the reality of death. In discussing the transmission, revitalization, and transformation of Chan Buddhism in modern East Asia, this inquiry is more relevant than ever. Ignoring its iconoclasm and iconic spontaneity, traditional Chan was understood within the Buddhist doctrinal framework as a path to awakening that traverses the six realms of cyclic existence toward a clearly defined goal. A path that does not liberate one from birth and death does not qualify to be Chan. Weizhao’s interpretation of the great matter of death that supercedes all other koans seems to allude to a total quietude that allows one’s Buddha nature to shine forth. In the eleventh-century Yiqing xingchuan, too, the great death seems to be equated with silent illumination. Rest and cessation are not some distant place, but imminently accessible. Danxia Zichun counsels the Chan student to “let go of all worldly concerns and sit totally still.” Susuki Roshi concurs: “Don’t move. Just die. Moment after moment. This is your last moment, so nothing can save you now. Not even enlightenment will help you now, because this is your last moment. So be true to yourself and express yourself fully.” The koan is whether “broad and penetrating comprehension” can arise from a simple absence of mental activity or whether it expresses something beyond that. This paper will apply a multi-disciplinary approach to explore the social, religious, and psychological implications of Chan Buddhist thought and practice related to death and dying, both in Chinese literature and in contemporary Chinese communities.