Introduction: Education and training of junior staff is a core responsibility of consultant surgeons and surgeons in training, with assessment of learning doctors forming an important part of this role. Many clinical educators, however, feel unprepared or unwilling to report unsatisfactory learner performance. This ‘failure to fail’ phenomenon was first described over 40 years ago, and an understanding of how it occurs and how it may be avoided is critical to both preventing failure, and in remediating underperforming learners. Methods: A review of literature relating to failure to fail was conducted through EMBASE, CINAHL, and MEDLINE. Articles were reviewed for relevance, and those deemed suitable were included in the review. Key concepts in the application of failure to fail in surgical education and training were identified. Results: Of 167 screened articles, 24 were relevant to the topic of failure to fail in surgical education. The concepts identified were: 1. How to identify failure, 2. How to address failing learners, 3. How failure to fail occurs, 4. What are the consequences of failure to fail, 5. How to prevent failure to fail. Conclusions: The key concepts in understanding failure to fail and its consequences were common across the literature. With teaching being a core competency of the surgical training and professional continuum, an approach to the failing learner is important to educators at all levels to ensure patient safety through appropriate assessment and remediation of learners.