Despite an abundance of literature about knowledge and outsourcing the theoretical concepts and research findings are not immediately applicable in practice. In this paper we present the insights and the effort used to find a way to support knowledge transfer in outsourcing. More specifically, we aim to support operational managers responsible for outsourced IT activities in carrying out the concrete task of knowledge transfer planning and execution. We report from a longitudinal project conducted in a major financial company headquartered in Denmark and an offshore development center located in India. We identify the three main knowledge transfer challenges experienced by the case company. The identified challenges inform the design of a systematic five-step approach to the company’s knowledge transfer. Our main contribution is to illustrate how extant research can be applied to understand and solve a particular company’s knowledge transfer challenges in a way that fits with the company culture.