This case describes how an assessment task for a postgraduate unit (Information Systems in Business) was developed and delivered using the virtual world platform Second Life. Students investigated and reflected upon the appropriateness of particular technologies for organizations and in particular for an insurance company. The assessment task was undertaken twice during 2010 and reflections from the students on their learning in relation to this task are included. The lecturer also reflected on the students' learning and application of technology skills, and these two sets of reflections were triangulated with data collected in a survey of the two student cohorts. Emergent themes from the data included graphics and interface, ease of use, game versus virtual world, business context usefulness, and social network characteristics, and these are discussed. Implications for designing authentic learning and assessment tasks with virtual worlds in a higher education context are explored in this chapter. The authors conclude that virtual worlds are a suitable application to support students learning of content knowledge, providing the technology is constructively aligned with the curriculum.