This paper describes a retrospective study of the big budget National Programme for IT (NPFIT) in the UK. The project is seen through the lens of the national newspapers and analysed via the Cynefin model. A set of success factors in health information system (IS) initiatives are derived from the literature, 584 newspaper stories drawn from the period October 2002, when the NPFIT programme began, until the end of 2012, are analysed using a multi method approach to identify gaps between real information systems issues and reporting. Results suggest that gaps between media reporting and success factors are captured by the less tangible (complex and chaotic) aspects of the Cynefin framework. Further, newspaper articles skirted around many human aspects of system development that were prominent in the IS literature such as of change management and user acceptance. The most commonly reported domain moved from known to chaotic as the project progressed.