Objective: This paper describes the literature that underpins the work of a funded teaching and learning project (Student Success Toolbox project). This project focuses on how effective socialisation supports can be utilised to support flexible learners as they enter higher Education (HE) and create new student identities, such that the ‘entry shock’ they experience does not result in an early exit from HE. Method: The project addresses the problem of effective flexible learner transitions into HE, during the study-lifecycle’s initial stages, and is creating a suite of appropriately designed, openly available digital readiness/preparation tools, based on an analysis of existing literature. Result: The suite of tools is currently being created, with tool effectiveness being evaluated through small pilot evaluations with flexible learners. Conclusion: Many flexible learners succumb to ‘entry shock’ and exit early from HE, which is a problem both globally and within the Irish context. The existing literature indicates that this crucial transition period may be enhanced by the availability of digital readiness/preparation tools, which actively socialise these students and scaffold them in their formation of a student identity.