In Australia coeducation dominates government schooling, with single-sex institutions usually being the preserve of selective government schools and private, often elite, institutions. For marginalised young people who 'drop out' or are forced to leave the coeducational mainstream system, flexible and/or non-traditional schools provide alternative pathways. Such schools are primarily coeducational. This paper draws upon data from two flexible/non-traditional schools in Australia that attempted to address the issues of educational disengagement via the provision of single-sex schooling: Fernvale Education Centre and Lorem School. The data are insightful with regard to these two very different gender and education paradigms and to their associated discourses about masculinity and femininity. The paper will identify the ways in which these schools both reproduce and challenge dominant constructions of gender within the context of responding to disenfranchised/disengaged young people.