Medical residents are valuable sources of information about the quality of frontline service delivery, but if they do not speak up, their ideas, opinions, and suggestions for improving their work practices cannot be considered. However, speaking up can be difficult for residents. Therefore, the authors have explored both what helps residents speak up about organizational barriers and opportunities to improve the quality of their work and what hinders them from doing so.The authors conducted an exploratory qualitative interview study with 27 Dutch medical residents in the Netherlands in 2016. They used the critical incident technique for data collection and the constant comparison method of the Qualitative Analysis Guide of Leuven for data analysis.Three types of incidents in which residents considered speaking up are described. The authors identified two main considerations that influenced residents' decisions about speaking up: Is it safe to speak up, and is speaking up likely to be effective? Residents' decisions were influenced by personal, team, and organizational aspects of their situations, such as supervisors' open attitudes, hierarchy, duration of clinical rotations, organization size, and experiences (either vicarious or their own).Findings from this study indicate that residents tend to be silent when they encounter organizational barriers or opportunities to improve the quality of their work. Perceived effectiveness and safety are important forces that drive and constrain speaking up. The authors provide important starting points to empower medical residents to speak up about their suggestions for change.