The creative use of e-learning to facilitate the transition to and from university is the subject of this chapter. It describes a pilot, online transition to university project entitled Click Around ECU (Edith Cowan University) and an online, generic skills and career planning project called Careering Ahead in Health Promotion. Both projects are informed by authentic learning pedagogy that seeks to engage students in problem solving and learning by engaging in purposeful activities. The projects also seek to empower students to decide for themselves what they need to know about the transition process. Each project is described in the context of its implications for e-learning. The core thesis is that e-learning produces creative outcomes when embedded in appropriate pedagogy.