The ability to communicate persuasively is an important managerial tool. Surveys of both students and employers underscore the importance of oral and written communication skills and persuasion to successful careers in business. Writing persuasive documents to customers, subordinates, superiors, or stakeholders requires the ability to analyze the audience, marshal arguments, use evidence in a persuasive manner, and use an appropriate tone. Students must learn how to create discourse appropriate to rhetorically persuasive contexts if they are to become successful managers. This assignment presents a fictitious case about a wrecked Jeep Cherokee and asks students to challenge the insurance company settlement. Their task is to develop arguments around the evidence collected from newspaper advertisements to persuade the insurance company to pay more for the car. This assignment aims to teach students to argue persuasively using evidence to support their assertions; to learn clear logical writing that focuses on the audience and uses strategies for persuasion; and to incorporate theory into a very practical scenario and understand the importance of purpose, audience, and situation. A list of references and suggested readings is included.