Background: Educational domains such as pedagogy or psychology have embraced the philosophy that "allowing failure" in training and practice is essential to learn. In clinical training, however, allowing learners to fail is not explicitly discussed as a strategy, possibly due to the negative implications for patients. Therefore, we do not know whether clinical supervisors allow trainees to fail for educational purposes and, if so, how this supervisory strategy is used. Methods: To inform research on this topic, we conducted a narrative review to understand what was known about this educational strategy in postgraduate medicine. Results: Analyzing the selected literature, we found no studies directly exploring the question of clinical supervisors allowing failure as an educational strategy. However, related literature on resident errors suggested that trainees perceived their own errors to be highly instructive and that factors such as a sense of responsibility and emotional response influenced the educational impact of these errors. Conclusions: The lack of discussion in the medical education literature regarding allowing failure for learning suggests that we need research into the nature and extent of this supervisory strategy which may hold educational benefits but must be employed in a manner that upholds patient safety and safeguards trainee resilience.