The process of decision making regarding the outsourcing of various tasks in an enterprise’s value chain involves consideration of a number of important economic trade offs. Outsourcing decisions in the past have typically been of a strategic nature involving long-term commitment. However, given the emerging technologies of Web services and the growing variety of service providers it seems feasible to utilize the Internet’s ubiquity and pervasiveness for outsourcing at least more simple tasks dynamically in a call-by-call manner. However, to make the required decisions in each instance without having to manually assess the quality of each offer an automatic quality assessment based on a mutual service level agreement is essential. In this paper we will investigate the necessary mechanisms and demonstrate their feasibility in a real world use case scenario.