Role-play can be a powerful educational tool, especially when dealing with social or ethical issues. However while other types of education activity have been routinely technology-enhanced for some time, the specific problems of supporting educational role-play with technology have only begun to be tackled recently. Within the eCIRCUS project we have designed a framework for technology-enhanced role-play with the aim of educating adolescents about intercultural empathy. This work was influenced by related fields such as intelligent virtual agents, interactive narrative and pervasive games. In this paper we will describe the different components of our role-play technology by means of a prototype implementation of this technology, the ORIENT showcase. Furthermore we will present some preliminary results of our first evaluation trials of ORIENT. © 2009 Springer.