This chapter explores vulnerability, courage, and grit in turn, considering their relationship to one another and to the task of educating for emotional virtues and for social justice. Resilience and mindfulness in education are often recommended to make vulnerable or at-risk youth less vulnerable, to mental or emotional disturbance, poor academic achievement, drop out, and related concerns. Yet this chapter argues that there is a bright side to vulnerability, and good reason to question common conflations of it with entirely negative experiences and feelings. There can be a positive role for particular kinds of experiences of vulnerability, generally within communities, and particularly in education. On the other hand, courage is normally prized in society, and has been promoted in education. However, to be understood as a virtue, courage must be tempered, so that it is not reckless, careless, or brash. Grit is a combination of passion and perseverance.