This paper reports on a project that has sought, through the production of OERs, to address the problem of effective transitions and the foundations for student success during initial stages of the study lifecycle, with a specific focus on flexible learners. Drawing on the literature, the experience of major international providers, and a set of overarching guiding principles, this project adopted a design-based methodology (Reeves, 2006; Wany & Hannafin, 2005) to develop eight digital readiness/preparation OERs, along with a guide to supporting new flexible learners, which will inform institutions/discipline teams on how to effectively augment and deploy these OERs. The tools were developed by taking tools that already existed in this space and: taking inspiration from them; augmenting them; and improving upon them in order to produce this project’s set of tools. This project’s OERs are available under the most open Creative Commons License. Enhancing retention and completion rates of flexible learners, defined here as undergraduate adult, part-time and online/distance students, is a significant problem. In the Irish context undergraduate part-time students represent 17% of all undergraduates (HEA 2012). Gallie (2005) notes that some reports put student attrition in online distance education delivery to be as high as 80%. This tallies with the UK Open University’s reported completion/graduation rate of around 22% (Woodley and Simpson 2014), as compared to a (British) national graduation rate of 39% for part-time students. A premise of the project is that the foundations for student success are laid early in the study lifecycle (Armstrong, 2015), and that insufficient attention has been given in the literature and within institutions to the importance of the period before learners formally commence their studies. A related underlying assumption is that this crucial transition period may be enhanced by the availability of appropriately designed digital readiness and preparation OERs, which help to scaffold prospective students and those about to embark on part time or online/distance study for the first time. This project is funded by the (Irish) National Forum for the Enhancement of Teaching and Learning in Higher Education (http://teachingandlearning.ie), and involves four Irish Higher Education partners.