That Dragon, Cancer represents one of the first notable biographical documentary games to address terminal illness and personal loss. This article highlights how the actionable properties of games are repeatedly reversed to generate a thoughtful reflection on the impact of medical jurisdiction over the dying and its regulation over the end of life. Liberating the medium’s reliance on certain commonplace and overused design principles, That Dragon, Cancer seeks to foster empathy, and urge care, hesitation and preservation rather than progression, advancement and winning states. The resultant game is a poignant digital commemoration of the game creator’s son, Joel, whose life was affected and curtailed by cancer. In addition to being a document of parental grief and loss that offers an emotionally resonant and candid articulation of the effect of disease on the trajectory of life and biography of a child, this article also reasons that the game comprises Joel’s constructed post-self, allowing his life to be extended post-mortem.