This paper presents selected findings from a 5-year design-based research case study of the evolution of an online role play that allows postgraduate students to explore the complexities inherent in land rights negotiations between indigenous peoples and others. In the context of Laurillard's (2002) conversational framework and a design-based research methodology, diverse private and public discussion forum spaces were created for group negotiations on a learning management system (LMS) platform. Our analysis of the conversational framework structure in the evolved role play showed that all four stages - discursive, adaptive, integrative, and reflective - were evidenced, with the adaptive and integrative stages cycling through multiple times. The online role play, whilst implemented as a simple virtual world, facilitated personal, deep and socialised learning experiences focused on consultation, negotiation and decision-making. We also found that student anonymity was not necessary for full engagement in role play, and that students chose to incorporate communication technologies outside the LMS into their learning activities. This research shows that with a strong pedagogical design, and attention paid to an evidence-based iterative improvement cycle, online role plays can provide powerful collaborative learning experiences.