This paper examines C.S. Lewis's "A Grief Observed" (1961), focusing on two intertwined tensions: the silence of sacred texts on the possibility of meeting our loved ones again in the afterlife and the impossibility of fully reconstructing the voice and identity of the deceased—whether in religious narratives or digital simulations. Using a semiotic approach and reflecting on the crisis of the indexical function of the voice in the post-digital age - that is its capacity to point to a specific body or source - , I argue that both religion and grief-related technology fall short in providing comfort to the bereaved. Representations of the deceased— from Dante and Beatrice's reunion to contemporary digital simulations — fail to capture the lived individuality of those who have passed. Lewis's reflections highlight this gap: surrounded by silence, he was at one point tempted to contact his late wife, H., through a medium but ultimately declined, honoring a promise to her. In contrast to the formula of the image as a site of resurrection that Roland Barthes (1980) later made famous, Lewis emphasized that hearing her voice— the authentic trace of her presence— remained the only true consolation. Today, technology makes such auditory encounters possible, raising questions about the limits of digital resurrection. This paper uses Lewis's words as a lens to explore what remains irretrievable in grief, even in an age of technological simulation, arguing that his words anticipated contemporary anxieties about AI-generated voices. Both religious language and grief technologies promise comfort but deliver only signification, drawing on Massimo Leone's concept (2026) that silence can act as a semiotic device, blurring the boundaries between expression and non-expression.