The move to agile software development methodologies has generated great enthusiasm. The emphasis on team-oriented development and reliance on people rather than predefined processes is transforming software development into a socio-technical process. Through the lens of a real-world project we examined the difficulties experienced when an IS development project shifted from a structured waterfall approach for upfront requirements gathering to a Scrum agile approach for the development activities. We specifically look at the agile values and principles of ‘people, working software, end-user involvement and responding to change’. Although the transition was successful in practice, in principle the project failed. The empirical case study evidences the characteristics involved and we put forward critical factors of the preparation of the environment (i.e. adequate Scrum training), effective communications (i.e. consensus on a standard working context and sufficient time for testing), optimal team structure (i.e. personalities) and effective team leadership to inform future development practice.