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This chapter draws on longitudinal case study research that focused on the experiences of hospitality employees working in a UK university who worked split shifts in the morning and evening while completing NVQ 2 and 3 apprenticeship training. We show how fragmented working time (Rubery, Grimshaw, Hebson, & Ugarte, 2015) rather than long hours led to the apprenticeship training further eroding an already blurred work-life boundary as workers were required to complete training activities in their non-work time which for them is during the middle of the day. We argue current depictions of the positive impact of training and development on low paid workers are decontextualized from the challenges and priorities of workers whose work-life interface is already complex because of working fragmented hours across the day. This is complicated even further by the dynamic and evolving experiences of workers themselves as they experience the highs and lows of combining paid work and training. We situate the research in the context of wider conceptual debates that call for a more inclusive approach to research on the work-life interface (Warren, 2021) and highlight implications for HR practitioners who want to offer such opportunities to low paid workers in sectors such as hospitality, while also recognizing the complex challenges such workers may face.