This paper presents the findings of a research project on older workers transitioning into work as vocational educators through online undergraduate university study. The study involved interpretive phenomenological analysis of the experiences of 10 older learners. Their experience of online learning was found to be shaped by diverse influences and to comprise three distinct but interrelated elements: their use of technology, their use of hypermedia and their independent learning. Challenges raised by each of these elements called for a distinctive response from the university, respectively: short-term, readily available technical advice and support; tutoring to develop Web navigation and exploration skills, or the provision of selected readings; and opportunities for online or face-to-face dialogical engagement with others. Recommendations for the online provision of higher education for such learners, then, pointed to the need for an appropriately distinctive response to challenges in each of the three elements: the use of technology calling for individualised and immediate responsiveness to learner issues; the use of hypermedia calling for aggregated advice and resources prepared in advance; and independent learning calling for the prior structuring of opportunities for interactive engagement. Further research is suggested focusing on the relative cost and effectiveness of different approaches to addressing those needs.