This article concerns the investigation of management issues in the due diligence and contracting phase within information technology outsourcing contracts. The information technology outsourcing life cycle is used as the flow structure for the investigation. The associated user expectations that occur in the due diligence and contracting phase of the information technology outsourcing life cycle are identified. Following the identification of the management and user expectation issues in the due diligence and contracting phase of the outsource life cycle, the "Coetzee solution framework is used to ensure that the identified management problems are addressed in a structured approach.