Governments around the world are investing in large scale information and communication technology projects that are intended to modernize and streamline healthcare through the provision of nationally accessible electronic health records. In this way, they hope to 'tame' the complex 'wicked' problems facing healthcare, such as rising costs and fragmented delivery. However, these projects often encounter difficulties. Using a case study of Australia's 20-year journey towards a national electronic health record system, we show how these projects can ironically take on the characteristics of the 'wicked problems' they are intended to solve, and how a failure to recognize and cope with these 'wicked' characteristics can lead to waste, conflict and frustration among potential users. We suggest some alternative approaches to the management of large-scale ICT projects in healthcare and other public service sectors that deal with complex, sensitive data.