In this article, we interrogate the policy assumptions underlying a significant South Australian public education re-engagement initiative called Flexible Learning Options, formulated within South Australia's social inclusion policy agenda, beginning in 2006. To this end, we applied Baachi's 'What's the Problem Represented to be?' policy analysis framework to a historical range of departmental Flexible Learning Options policy documents and evaluations to uncover how Flexible Learning Options (1) understands the problem of early school leaving, (2) defines the notion of being an 'at risk' young person and (3) interprets and enacts the intervention process for young people identified as 'at risk' of early school leaving. Our policy analysis indicates re-engagement in learning - as measured by improved retention - to be the key Flexible Learning Options policy driver, with schools 'silently' positioned as a significant part of the retention in learning problem. The Flexible Learning Options engagement in learning intervention directed at 'high-risk' students' works to remove them from schools into places where personalised support and an alternative curriculum are made available. 'Lower risk' students are given a combination of in-school and off-school learning options. Our What's the Problem Represented to be? analysis also reveals that (1) the notion of 'risk' is embodied within the young person and is presented as the predominant cause of early school leaving; (2) how the educational marketplace could work to promote Flexible Learning Options enrolment growth has not been considered; (3) schools are sidelined as first choice engagement options for 'high-risk' young people, (4) secondary school redesign and family intervention as alternative reengagement strategies have largely been ignored and (5) through withdrawal from conventional schooling, the access of many Flexible Learning Options to students to an expansive curriculum delivered by teachers within well-resourced school learning architectures has been constrained.