Information technology outsourcing (ITO) has gained a big share of the world IT service market. There are many studies about ITO vendor selection and contract management but a lack of understanding of the after-contract practices between the ITO parties. According to reported cases, many outsourcing failures have been due to either improper relationship management or the inability to meet customer expectations. For effective management of this long-term, inter-organizational relationship, there is a need to understand the features, affecting factors, expectations, and termination of ITO relationships so that the desired outcomes can be achieved and relationships can be sustained throughout the life of the ITO. Based on a dynamic view of outsourcing partnerships, the ITO relationship can be assessed by customer participation, joint action, communication quality, coordination, and information sharing. Prior studies have indicated that these ITO relationship features are mainly affected by business dynamics and the client’s IT competence. Organizations expect from the ITO mainly strategic, economic, and technological benefits. When conflicts exist between expected benefits and delivered outcomes, the relationship is more likely to be terminated. The above propositions were tested on all existing and changed ITO projects in Taiwan in the past twenty-six years. A total of forty cases were examined and the results show four kinds of IT outsourcing relationships: dependent, utility, partner, and subordinate. Different kinds of ITO relationships involve different expectations for the ITO services and require different types of management of the relationships. In the dependent type ITO, customers rely highly on ITO vendors for supporting strategic moves. Utility ITO customers use the ITO as a utility and measure vendors by cost performance. In the partner type ITO, customers consult the vendor for strategic business moves and urge the vendor to engage in technology innovation. The subordinate type ITO is characterized by customers who consider the ITO vendor as a sub-contractor of their IT department and leave decisions to the IT department. Terminations of relationships were mainly due to conflicts in the expected and delivered outcomes in the three ITO benefit areas. This study provides a useful instrument for assessing major ITO factors and understanding expected ITO outcomes. ITO relationship management requires a careful understanding of the expected benefits of the service and continuous monitoring of the business and IT environments.