Case-based discussions (CBDs) are structured, reflective reviews that assess clinical decision-making, communication, and professionalism within medical education, particularly in surgery. This critical review examines the validity, reliability, practicality, and role of CBDs as an assessment tool. CBDs demonstrate strong face and construct validity, given their alignment with real-life clinical practice. However, concerns regarding their limited content and predictive validity, inconsistency in assessment, and the lack of assessor training challenge their effectiveness. CBDs have practical value in assessing judgment and professionalism but are resource-intensive. Formative feedback provided through CBDs enhances student learning, while their summative nature guides progress. To optimize CBDs' effectiveness, formal assessor training and consistent evaluation are recommended. A combination of assessment modalities is necessary to cover the entire curriculum and ensure comprehensive trainee development.