A crucial factor for successful cybersecurity education is how information is communicated to learners. Case-based learning of common cybersecurity issues has been shown to improve human behaviour for prevention. However, some delivery methods prevent realistic critical appraisal and reflection of awareness. Conversational agents can scaffold healthcare workers’ understanding and promote deterrence strategies. The challenges of repurposing material to create a case-based agent were explored, and the ASPIRE process was modified. Heuristic evaluation from 10 experts in innovative educational technology resulted in the desired outcomes of usability, however Natural Language Understanding improvements were needed. Discussion of best practice when repurposing into conversational agents suggested modification of the ASPIRE process is feasible for future use.