Higher education is undergoing change, whereby technology is used to mediate learning for an increasingly diverse student population. Many choose flexible options studying online and at a distance to the university. Such policy directions have created an educational problem for students, namely how to manage this mode of learning while maintaining complex lives juggling work, home and study. This research formed part of an extended design-based research project studying the practical problem of health science students transitioning to online distance study. A subset of five students studying an undergraduate fully online nursing degree at a regional university was used to examine their engagement with an online orientation resource designed to smooth the transition to university study. Their digital footprints illustrating student access levels were combined with qualitative interview data to identify and interpret meanings about the way they encountered and constructed their study world. Findings indicated that technical aspects, lifestyle, interaction and academic supports created both barriers and enablers for this transition. The essence of the students’ experience revealed a complex study journey with multiple layers of transition. This involved adjusting to being a university student, managing the distance and online environment and re-positioning their occupational mindset. Their ability to manage these layers of transition was influenced by their self-regulatory skills. The variation in experiences evident through the eyes of these five students highlights the diverse patterns of engagement. Universities need flexible and varied approaches to enable successful transition for distance and online learners.