This paper examines the rise and fall of the Victorian education department's learning management system Ultranet. The Ultranet was conceived as a web-based portal that was designed to integrate and deliver on a range of policy objectives in the areas of student management, school networking and communication, and teaching and learning. Heavily promoted by the Victorian educational bureaucracy and the government, the Ultranet, which operated between 2010 and 2013, proved a costly failure and became the subject of an inquiry by Victoria's anti-corruption commission. This paper looks beyond the inquiry's focus on the conduct of senior departmental officials involved in Ultranet's procurement to examine the policy, technological and pedagogical contexts that framed the project. We argue that the project had its roots in pre-digital educational policy settings of devolution and entrepreneurship, which supported a transformative agenda focused on digital information and communication technologies. While the Ultranet software had fatal design and usability flaws, we broaden the scope of analysis to argue that the project rested on problematic assumptions about the digital literacy and connectivity of parents and teachers, and the viability of a technology-based response to risk and privacy embodied in a 'closed' network, that compromised the venture from its inception.