In farming, the outcome of critical decisions to enhance productivity and profitability and so ensure the viability of farming enterprises is often influenced by seasonal conditions and weather events over the growing season. This paper reports on a project that uses cutting-edge advances in digital technologies and their application in learning environments to develop and evaluate a web-based virtual ‘discussion-support’ system for improved climate risk management in Australian sugar farming systems. Customized scripted video clips (machinima) are created in the Second Life virtual world environment. The videos use contextualized settings and lifelike avatar actors to model conversations about climate risk and key farm operational decisions relevant to the real-world lives and practices of sugarcane farmers. The tools generate new cognitive schema for farmers to access and provide stimuli for discussions around how to incorporate an understanding of climate risk into operational decision-making. They also have potential to provide cost-effective agricultural extension which simulates real world face-to-face extension services but is accessible anytime anywhere.