Studies show that the psychological impact of a death in the school community may lead to impairment of student academic performance, reduction of attention span, behaviour problems, and mental health crises such as depression. However, there is also a high level of discomfort with openly discussing issues of dying, death, loss, and grief within the school community, especially among younger children. Educators and other school personnel often acknowledge that they feel ill-equipped to address the emotional needs of bereaved students. One school social worker told us, “The bulk of my time with students is dealing with issues of loss and grief, and I have had no training or tools to help me with this.” The Compassionate City Charter identifies Schools as an essential part of our communities, connecting intergenerational families through their children’s daily education. By creating compassionate school communities, together we can more effectively support school children and others experiencing loss and grief, including their families.