Mutual support and dialogue across secondary and tertiary English is vital work in urgent times. In this article, the authors examine Australia's secondary-tertiary English education nexus, building on previous scholarship to explore points of connection and disconnection with a view to identifying sustainable ways of supporting points of interchange. Using the framework of complexity theory, they identify nested and overlapping sets of educational systems. Acknowledging complexity in the endeavour to build dialogue across sectors is one of five principles the authors outline in terms of proactive ways for building further dialogue. In English education, complexity exists at both the macro-level and the micro-level. Macro-level complexity involves but is not limited to the national curriculum, peak bodies for English, and the academic discipline, broadly conceived; micro-level complexity involves local community interactions, particular university environments, and the enacted secondary curriculum at any given school or site. The authors point to regional Australia as a place where interaction across the secondary-tertiary divide sometimes spontaneously occurs; ultimately, they make recommendations that larger structures and supports are needed to ensure this kind of interaction is both sustainable and more widespread.