The dominant view in the information technology (IT) strategy literature implicitly or explicitly incorporates a normative model of dynamic alignment in which business strategy is seen as the primary driver of strategic adaptation. This paper describes and analyzes a case study of the strategic application of IT where success emerged via a different process. As well as providing evidence of a path to strategic fit that is rarely discussed in the literature, the case points to mastery and the management of risk as critical factors in the process of IT-based strategic change.