<p>In recent years, philosophical research on the phenomenology of grief has gained momentum. This research shows that social, material, and technological resources in our socio-culturally structured environments shape the structure and unfolding of grief experiences. As new Artificial Intelligence (AI) technologies have entered our lifeworlds, including chatbots based on Large Language Models and AI-generated virtual environments, new research questions afford our philosophical attention. How do contemporary AI technologies influence and shape grief experiences? What are the risks and benefits of integrating AI technologies into the navigation and negotiation of bereavement and non-bereavement losses? This Special Issue titled “Grief in the Digital Age” addresses these questions by showcasing cutting-edge research on grief in the digital age at the intersection of phenomenology, philosophy of mind, the cognitive sciences, and the philosophy of AI. In this Introduction, we briefly summarise the epistemic aims of this Special Issue and provide a thematic overview of the contributions. We conclude by reflecting on avenues for future research opened up by this Special Issue.</p>