Learning engineering provides both a practice and process for solving educational challenges. While the circumstances of each challenge require a unique application of learning engineering, the learning engineering process was designed in such a way to provide guidance across a broad range of contexts. In this paper, the learning engineering process is articulated from the perspective of the developers of online courseware used in higher education. Within this use-case, we exemplify how an initial learning engineering process for the creation of the courseware provided a starting point for iteration, and in this instance, the beginning of an entirely new process on instructor enactment of that courseware. Whereas the initial challenge was to develop the courseware environment, this emergent challenge now focuses on understanding and addressing contextual factors that affect the successful instructor application of the courseware learning environment at scale.