Future deliveries of payloads to orbit are likely to utilize space transportation services that employ a fleet of reusable launch vehicles. To achieve this capability will require the investment of billions of dollars. Such sizable investments will require the formulation of detailed business plans that demonstrate the financial viability of the proposed business and that the business can function within an acceptable level of risk. Besides coping with the normal business risks associated with achievable level of technical performance, demand for launch services, competition, etc., the business must also cope with the risks associated with transportation system failures and delays. This requires the development of a viable risk management plan. This paper is concerned with describing a risk management scenario that can demonstrate and provide an assurance, at the time that investment decisions must be made, that the necessary insurance cover at affordable prices will be available.