Digital transformation within higher education learning and teaching is a wicked problem, one of complexity, involving multiple moving parts and interdependencies (Marshall, 2018). Current conversations tend to coalesce around whether transformation is a pedagogical problem or a technological problem. However, when one takes a pedagogy-first approach, the contextual forces around the technology are ignored (Dron, 2012), and the same is true in a technology-first approach. This research aimed to take a more holistic approach to explore the interdependencies between context, pedagogy, and technology in higher education. To study how they associate and, more importantly, how they influence each other, producing actionable knowledge for designing and supporting effective technology-enabled learning environments. Digital learning and teaching knowledge is often explored through the Technological Pedagogical Content Knowledge (TPACK) framework (Mishra & Koehler, 2006), especially in K-12 learning environments and teacher education programs. While TPACK can assess teacher beliefs about pedagogical and technical knowledge, little has been done to explore how those working in higher education institutions apply this knowledge within their design approaches to build learning and teaching environments with their students. The study of learning and teaching environments is often a separate line of inquiry. Digital learning environments and the actions within are often explored through the use of the Community of Inquiry (Garrison et al., 2000) framework. This study combined these two lines of inquiry by developing an evaluative tool, a new deductive codebook, that drew on these two frameworks within these disparate areas of educational technology research. This codebook brought together aspects of context, technology-enabled design, and the learning and teaching experience to understand digital teaching and learning practices within their lived environments. This study sought to understand these practices from both an academic and student perspective by using a case study methodology to generate rich qualitative data for five academics. Each academic’s design process was captured through a mixed-methods approach, including survey responses, semi-structured interviews, and collection of online course artefacts (course outline documents and course websites). Their course designs and communication of their designs were analysed through both content and network analyses. Focus group interviews with their students were also conducted to understand their perspectives on the coursework and how the students understood the academics’ intentions for their designs. Through this multi-layered lens, this study found that while the academics were able to describe their pedagogical and technological approaches towards course design, their ideas were not always linked to how the actions of students or themselves contributed to the overall realisation of the learning experience. The context within which academics design courses also had significant positive and negative influence on their approaches towards technology-enabled design. The study also identified that the communication of designs to students did not always reflect the intent of the design, express the student’s responsibility within the designs or set them up for success in navigating the learning and teaching environment. As a result, students struggled to discern their responsibilities within these environments. The student data also highlighted that they bring their own understandings of pedagogy and technology, understandings that can be at odds with the academics’ own ideas or intentions for the learning and teaching environment, which can constrain the perception of success of the course for both the academics and students. This research complements and builds on understanding the highly contextual nature of academic coursework as a complex system. The combined use of the theoretical frameworks in a qualitative codebook highlighted the importance of investigating academic design knowledge in action. Revealing that the gaps in teacher knowledge do not lie so much between pedagogy and technology rather lie in the effective realisation of the learning and teaching experience with students as active participants. The implications support further research in how academics build and use this knowledge within their course designs and how contextual forces influence how knowledge is applied to create and sustain learning environments with their students.