This practice report discusses the development of the Head Start Online MOOC. This initiative targeted flexible learners, defined as adults engaged in part-time or online distance learning, during the initial stages of the study life-cycle. Drawing on the literature, the experiences of major international Online and Distance Learning (ODL) providers, and a set of overarching design principles, the MOOC (Massive open online course) was developed with a suite of digital readiness tools at its heart. These tools were combined with other supporting materials in order to deliver a comprehensive pre-entry socialisation course. A small pilot of Head Start Online ran over five weeks with 150 people enrolled and 50 going on to receive a certificate of completion. The feedback received, albeit limited by the numbers of respondents, indicates that a course that strategically uses digital readiness tools can have a positive impact on new and prospective flexible learners.