This paper describes an externally funded, by Ireland’s National Forum for the Enhancement of Teaching and Learning in Higher Education, research and development project designed to address the problem of effective flexible learner transitions into higher and continuing education. The project is a collaboration between four Irish Higher Education Institutions: Dublin City University (lead partner); Maynooth University; Dundalk Institute of Technology; and Institute of Technology Sligo. The project targets adults engaged in part-time or online/distance-learning during the initial stages of the study-lifecycle. Enhancing retention and completion rates of this group of life-long learners is an acknowledged concern both globally and within the Irish context. The literature suggests this crucial transition period may be enhanced by the availability of appropriately designed, freely available and strategically focused digital readiness/preparation tools, which scaffold both prospective students and those about to embark on study for the first time. Drawing on the literature, the experience of major international online/distance providers, and a set of overarching guiding principles, this project adopts a design-based methodology to develop eight digital readiness/preparation tools, along with a guide to supporting new flexible learners, which will inform institutions/discipline teams on how to effectively deploy the tools. The paper describes each of the tools and discusses the rationale for their development and how they can be used under a Creative Commons License (CCL) to support flexible learners through key transitions in the early stages of the study lifecycle.