A method and system for optimizing the interaction and execution of multiple service tasks associated with a logical transaction. The multiple components or “legs” of the transaction consisting of tasks executable by a computing service or software as a service (SAAS) endpoint are identified. The system determines a strategy type or belief level associated with each of the service tasks included in a transaction. The belief level may be categorized as either “optimistic” or “pessimistic” based on one or more performance parameters (e.g., a probability of failure of a service and an expense associated with a failure of the service) derived from historical data associated with a particular transaction or service task. A sequence of execution for the multiple service tasks associated with the transaction is determined based at least in part on the belief level associated with each of the multiple service tasks. In one embodiment, one or more unordered service tasks classified as pessimistic are performed before one or more unordered service tasks classified as optimistic.