A method and system for managing fleet health of vehicles comprises gathering environmental data for potential mission locations. A data processing system collects vehicle data, including historical use data and maintenance data associated with corresponding vehicular components of vehicles within a fleet. A mission planner establishes a list of candidate missions for the fleet of vehicles. A stress module assigns a stress severity indicator to the established candidate missions based on the environmental data. The mission planner matches vehicles to corresponding missions based on the collected vehicle data and the stress severity indicator such that the matched vehicles are likely to complete the missions with a desired degree of reliability.