The stigma of underperformance is widely acknowledged but seldom explored. 'Failure to fail' is a perennial problem in health professions education, and learner remediation continues to tax supervisors. In this study, we draw on Goffman's seminal work on stigma to explore supervisors' accounts of judging performance and managing remediation in specialty anesthesia training in Australia and New Zealand. In doing so, we focus on what Goffman calls a "stigma theory" to explain the supervisors' reported practices. We performed a secondary analysis of nineteen interviews originally gathered using purposive sampling to explore how assessment decisions were made. We conducted a theory-informed thematic analysis of the supervisors' accounts to identify signifiers of stigma and underlying structures and beliefs. From both deductive and inductive analysis, we developed themes that demonstrate how the stigma of underperformance influences and is induced by supervisors' reticence to discuss underperformance, their desire to conceal remediation, and their differential treatment of trainees. We also found that accounts of trainees 'lacking insight' resembled stigma-induced stereotyping. We argue from our data that our cultural expectations of perfectionism propagate a stigma that undermines our efforts to remediate underperformance and that our remediation practices inadvertently induce stigma. We suggest that a multifaceted approach using both individual and collective action is necessary to change both culture and practice and encourage the normalisation of remediation.