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. Informed by a comprehensive review of existing literature, and an analysis of the existing tools in use internationally, the Student Success Toolbox project has produced eight digital readiness and preparation tools (http://studentsuccess.ie/the-toolbox/). A basic premise of the project is that the foundations for student success start early in the study-lifecycle (Yorke & Longden 2004). A related assumption is that this crucial period may be enhanced by the availability of appropriately designed digital readiness/preparation tools (Currant and Currant 2009). The project’s tools are Open Educational Resources (OER), made available to institutions/programme teams with the most accommodating Attribution (CC-BY) Creative Commons Licence. Alongside the tools there is a guide on how to use the technology solutions as part of a strategic socialisation program and, where appropriate, directions on how to technically augment the tools to personalise them for a specific institution, program or cohort of learners. This participatory workshop will explore key points relating to the factors that impact on flexible learner transitions into Higher Education, and on their success in the first year. The workshop will then examine the digital readiness tools developed for the Student Success Toolbox project with a focus on: the purpose for which they have been designed; at what stage(s) of the study life-cycle the tools can best be utilised; and the degree of customisation that must necessarily be carried out before the tool can be used by a particular programme team/institution/support service unit. Finally the workshop will explore how some or all of the digital readiness tools can be used in combination as part of an effective flexible learner socialisation plan.