Online role-plays have been celebrated for providing an environment which allows for high quality learning. Innovative approaches have been embraced in foreign language studies, especially in countries where a great distance to the target country needs to be overcome, not only to expose students to the target language but also to provide them with a forum to apply and extend their newly-acquired language skills in creative applications outside the face-to-face classroom. This paper explores the design, application and evaluation of one of these innovative teaching and assessment strategies: an online role-play in German Studies at UWA. Complex educational objectives, as classified by Bloom and many others since, were the starting point for our design. However, despite all the ideal ingredients being included in the role-play, our evaluation transpired to be a corrective of sorts. It was intended to re-affirm that students appreciate the best-practice learning strategies which have guided the design and development of this role-play. Student feedback (gained through student surveys, vocabulary tests, classroom observations, as well as quantitative tracking of contributions) has been utilised to analyse the level of student engagement and their reflections on their learning in this role-play. Our findings suggest that even an ideally designed web-based role-play will not necessarily lead to a more effective way of learning, at least not from the students' perspective.