This is the second of two articles reporting on a longitudinal study of property law teaching in Australia. The focus of this article is the changing approaches of property law teachers to assessment, skills and outcomes. As a general observation, property law teachers appear to want to move beyond the traditionally doctrinal focus of the curriculum. They recognise the importance of ensuring students are equipped with the practical skills needed to work in a profession with a strong transactional focus. Several respondents also expressed a wish to adapt the skills and learning outcomes in their property law units so as to embed a more critical socio-legal approach to the role of property law in shaping an increasingly uncertain future. The ideas presented in this article for how this might be achieved arguably extend beyond property law to legal education more broadly, thus presenting frameworks for adapting skills and learning outcomes that are truly future-oriented.