The decades-old legacies of segregation in Chicago have resulted in high rates of violence within the city’s marginalized communities. To mourn the loss of a loved one, youth have adopted innovative grieving practices. As more youth are engaged online, researchers have begun to examine how they share experiences of everyday life. However, there is a dearth of research exploring how Black youth use social media to grieve. Drawing on qualitative data from images collected on Twitter, we examine the role images on Twitter play in the grieving process of Black youth from communities with high rates of violence.