Universities face the challenge of developing undergraduate structural engineering students' design judgement. This study evaluates whether introducing 'learning from failure', centralised around 'real-world' case studies, serves to facilitate the development of engineering judgement in structural design. The study identifies the use of three characteristics of engineering judgement: diagnostic, inductive, and interpretive in the work of the first-year undergraduate structural design students. Thematic analysis, combined with a constant comparison method and the rigour of inter-researcher reliability, was used to develop coding and mapping to evaluate students' work. The majority of students correctly applied diagnostic engineering judgement to the definition of a problem for a failure case study; and displayed the inductive aspect of judgement. Students' interpretive understanding embraced multi-faceted considerations, with engineering practice, complexity in causality, and learning from history being dominant. Introducing case studies deepened students' enquiry, stimulating the development of a more nuanced understanding of structural engineering judgement.