This article elaborates the organizational literature’s process theory of compassion – an empathic response to suffering – which falls short of adequately explaining why and how compassion unfolds readily in some workplace situations or settings but not in others. We address this shortcoming by calling attention to the basic uncertainty of suffering and compassion, demonstrating that this uncertainty tends to be particularly pronounced in organizational settings, and presenting propositions that explain how such uncertainty inhibits the compassion process. We then argue that understanding the accomplishment of compassion in the midst of uncertainty necessitates regarding compassion as an enactment of courage, and we incorporate insights from the organizational literature on everyday courageous action into compassion theory. We conclude with a discussion of implications in which we underscore the importance of organizational support for the expression of suffering and the doing of compassion, and we also consider directions for future research.