This article interrogates the concept of articulation through its enactment in post-compulsory education systems in Australia. It presents an initial analysis of the challenges and opportunities that articulation holds for individuals and institutions in the higher education, vocational education and training sectors. Making pathways work for learners is a challenge, especially when formal learning is no longer undertaken in a hierarchically ordered, chronological sequence; instead, people engage in multiple learning and earning transitions throughout their lives. This article will explore the cross-sectoral, institutional and curriculum issues emerging from current articulation practices between one regional university and its joint activity agreement with a local vocational education and training provider. (Contains 2 tables.)