James River is a holding company that owns and operates a group of specialty insurance and reinsurance companies. Its largest segment, Excess and Surplus (“E&S”) Lines insurance, focuses on insureds that generally cannot purchase insurance from standard lines insurers due to perceived risks related to their businesses. Included in this E&S Lines segments is James River’s Commercial Auto Division. In 2014, James River ramped up its Commercial Auto Division by underwriting a new type of insurance policy that covered Rasier LLC (“Rasier”), a subsidiary of the ride-sharing company, Uber Technologies, Inc. (together with Rasier, “Uber”). Until that time, ride-sharing insurance had only covered claims incurred while ride-sharing drivers were transporting passengers for Uber, thus leaving a gap in coverage for accidents caused by ride-sharing drivers while they were not providing transportation services for hire but were still logged on to the Uber applications and available to accept a ride. Uber was James River’s largest contract and accounted for more than 25% of its premiums in 2019.