This case invites teams to prepare for a business war game to explore aspects of the competitive dynamics in the auto insurance market. In particular, the case offers opportunities to discuss segmentation strategies, data analysis, and the phenomena of adverse selection and the winner’s curse. The simulation is conducted as a tournament between four insurance providers, each represented by one competing team of students. In each round of the tournament, competitors simultaneously submit a tagline summarizing the insurers’ positioning statements and a price per exposure-unit for each of 4,000 customer groups. The case is accompanied by an Excel spreadsheet that provides historical information about the insurance risks of each customer group.