This workshop focuses on how flexible learners can be effectively supported through key transitions in the early stages of the Higher Education study-lifecycle: from thinking about study; making choices; the registration process; and through the first few weeks, using Digital Readiness Tools. Flexible learners are defined as adults engaged in part-time or online/distance learning. Enhancing the persistence of flexible learners is a significant problem both globally and within the Irish context (HEA 2012; Simpson 2005). Although the number of flexible learners in Ireland is low in comparison to other countries, at around 17% of undergraduates (HEA 2012), there are concerns about their ability to progress towards completion. Set against this backdrop, and with support from the National Forum for the Enhancement of Teaching and Learning in Higher Education [http://teachingandlearning.ie], the Student Success Toolbox project is an initiative by four partner institutions to address this problem through the creation of a suite of Digital Readiness Tools.