The current vertiginous rise of artificial intelligence has opened up new opportunities for digital immortality. In this paper, I critically examine griefbots—AI-driven chatbots built to chat again with deceased loved ones. Drawing on Freud, I argue for interpreting griefbots as “melancholic” media. The framework of my analysis is psychosocial and aims to unravel the complex—technological and psychological—interplay between griefbots and their users. After a first section dedicated to griefbots’ paradoxical sense of familiarity—both “hyperrealist” and incomplete—I locate the origins of their “melancholia” in their nature as digital objects, utilising the concept of the “digital ruin”, and in their usage of “traces”, only apparently similar to photography. Then, comparing griefbots to Winnicott’s transitional objects, I explain the psychological meaning of melancholia: a denial of loss that amplifies loss. Ultimately, I address griefbots as elements of a contemporary media-based “immune system” that risks turning itself into “autoimmunity”.