Concerns have been raised internationally about whether alternative learning programmes are producing low-skilled labourers for rapidly disappearing twenty-first-century jobs. Researchers claim that learners in alternative programmes are more at risk due to the focus on low-level vocational and basic skill attainment, with a lack of formal academic pathways available to them. This article questions whether and in what ways an alternative learning programme supports young people to achieve successful transitions to sustainable social mobility for informed citizenship through a holistic approach to learning; or if class stratification is being re/enforced through systems' accountability discourses. Hesitant hopes in alternative learning are explored through an ethnographic study of one alternative learning programme across five sites in regional Australia. Contextually, not-for-profit community agencies provide physical infrastructures as well as youth workers and volunteers, while a publicly funded School of Distance Education provides teacher oversight of the curriculum. Findings suggest that the theme of 'hesitant hope' is constructed through the analysis of the discourses of supporting wellbeing, life skill development and academic learning. These discourses facilitate further analysis of the concept of social mobility, suggesting a conceptual starting point for an engaging critique of the differing perspectives on how support could be providing these marginalised young people with a sense of hope for a socially mobile future.