While educational design research promotes closer links between practice and theory, reporting its outcomes from iterations across multiple contexts is often constrained by the volumes of data generated, and the context bound nature of the research outcomes. Reports tend to focus on a single iteration of implementation without further research to determine the generalisability of the outcomes to new contexts. This paper outlines a retrospective analytical approach used to capture the significant design features of an online orientation resource implemented in one university context, and then adapted for further exploration, design and evaluation at a second contrasting university. The educational problem studied was how to support health science students to overcome barriers of transitioning to online distance study. A conjecture mapping process aligned to the three phases of educational design research provided a framework to review the outcomes at the first university. This guided the research at the second university, including choice of the data sources during implementation. This process enabled the researcher to undertake a comparative analysis and evaluate the extent of generalisability of the resource to the second university, leading to refined design principles and a framework that illustrates the student transition process.