Design has often been described as optimistic (Kolko 2013). However, the COVID-19 pandemic has left a lasting impact on our wellbeing, community support, and healthcare services which has particularly affected already vulnerable and marginalised populations (Patel et al. 2020). For researchers working with these populations, the emphasis on positivity can feel harmful. In this paper, I propose the concept of design grief as a challenge to design optimism. This approach has been informed by a variety of sources: my research at Scotland’s Digital Health & Care Innovation Centre on stigma and trauma, my membership in the Magnify inclusive design and research community, and my identity as a person with chronic illness. It explores how designers and researchers can work equitably alongside participants to actively respond to trauma through open-ended, co-creative practices of grieving with.