This chapter summarises insights from a set of interviews with university leaders, shedding light on the challenges they face in integrating education, digital, and estates strategies for the purposes of enhancing support for learning and improving students' learning outcomes. Analysis of the interview transcripts and associated university documents revealed that although chief information officers and directors of estates are highly committed to meeting educational needs, they often find that requirements for new learning tools and learning spaces are poorly specified. Examining the problem more closely, we observed that there is a conceptual void at the point where educational, digital, and estates thinking should be converging. We found few signs of a shared, robust understanding of the processes through which desired educational outcomes are achieved or of the role of digital and material infrastructure in supporting such processes. In the second part of the chapter, we sketch an ecologically informed response to this problem. We identify ‘activity systems’ as appropriate units of analysis in the work of connecting educational, digital, and estates strategies. We also suggest that more inclusive approaches to creating, managing, evaluating, and improving complex learning environments are needed—offering participatory design-based research as an example.