The discourse of graduate employability skills includes emphasis on digital capabilities. Digital capabilities encompass an understanding of the new and emerging technologies that are driving significant change in business, government and society and by implication, the critical and creative thinking skills to integrate these contexts with the law. By contrast, the accredited law curriculum remains focussed on doctrine thus frequently relegating consideration of law and technology to discrete (elective) subjects. Further, the default method of teaching and learning doctrine remains a case method approach using hypothetical problems. Such an approach to curriculum is, at best, neutral about the relevance of new technologies and the skills required to analyse them in a legal context with consequences for contemporary and likely future employer expectations for law graduates to be prepared for practice. This article first establishes the imperative to incorporate digital contexts into the core law curriculum as a means of providing students with foundational skills for a changing workplace. Secondly, it presents the case for an enhanced approach to teaching legal problem solving. Beyond the backward-looking hypothetical fact scenario, it suggests that a future focused analytical mindset is integral to the lawyer’s suite of thinking tools. Finally, it provides a case study of a critical—and doctrinal—analysis of a recent proposal to fractionalise lots in a Torrens system in tandem with a blockchain. The case study illustrates the application of an enhanced problem-solving approach. It shows how the broader context of new technologies might be integrated into property law teaching through prospective problem-solving.