This article evaluates the challenges of modular redesign and the potential contribution of serendipity in legal education by advancing a “living” curriculum model. The archaeology of the curricular redesign process is excavated by exploring the conditions influencing and constraining curricular redesign. Whilst this study is primarily located within the theoretical context of curricular redesign, it is also rooted in both the practice of law and higher education literature. A key concern of this research is to consider the under-explored interaction between serendipity and curricular design with a particular focus on how the surrounding serendipitous conditions proved timely and welcome in creating an unanticipated opportunity for such redesign. There remains a surprising dearth of research evaluating the influence of serendipity in legal education generally and, more specifically, with respect to the challenges of module redesign and delivery. This article uncovers a research agenda with themes concentrated on the role of serendipity in curricular design and how “real world” relevance can be incorporated into module redesign and delivery. It is suggested that serendipity-sensitive curricula which acknowledge current debates within law and the contemporary contexts within which law operates enhance students’ capacity to recognise the relevance and applicability of their legal knowledge. By remaining alert to the potential for serendipitous innovation in curricular redesign and by re-engineering curricula to facilitate serendipity, legal academics can enhance the incorporation of “real world” relevance into academic teaching.