A wide variety of ‘alternative’ or ‘flexible learning’ programs have been developed in Australia aimed at (re-)engaging marginalised young people with education. With varied and complex relations to mainstream systems, these educational spaces are inherently contradictory, where participation affords ‘possibility’ but also entails ‘risk’ (Vadeboncoeur 2009). Alternative education operates as both a space of ‘refuge’ and of ‘containment’ (Nairn and Higgins 2011) with potential to offer differing visions of learning and life-itself (Kraftl 2013) but, in the case of provision for marginalised students, to also reproduce structural disadvantage (Smyth and McInerney 2013). Assumptions about valued and valuable educational outcomes underpin these discussions. Yet, outcome measures are often imposed on alternative education from the mainstream. Drawing on research conducted in a range of alternative/flexible learning programs around Australia, this paper adopts a relational socio-spatial perspective to explore what success looks and feels like for students, staff and community stakeholders. This analysis reveals the different scales and domains of success that matter to those involved in alternative education and how these valued outcomes are managed and negotiated in relation to mainstream systems. The paper seeks to contribute to a re-configuration and expansion of what counts as success in educational spaces.