BACKGROUND: Simulation-based education (SBE) has emerged as an essential modality for health professions education. One of the central tenants of effective SBE is reflective practice, typically guided by a facilitated debriefing. The debriefing conversation has the possibility of becoming a difficult conversation based on learner and situation-related factors. Difficult debriefing situations may threaten the learning environment, thus requiring an appreciation and understanding of the various ways that learners may react adversely to simulation and debriefing. AIM: This article provides a review of the various phenotypes of difficult debriefing situations and a toolbox of proactive and reactive strategies to help guide the simulation educator to manage these situations, with the ultimate goal of achieving learning objectives.