The paper is a cross-case analysis of identity development of youth throughout their first year attending two alternative high schools. Alternative schools fall in an interesting space of being able to provide innovative and supportive opportunities that are different from mainstream schooling, yet also alternative schools are part of a mechanism for sorting youth on the margins of education (Vadeboncoeur, 2009). This creates a complex space for youth identity development. This study examines the interaction of youth and alternative schools, focusing on the process of identity development and the resources in school that help support that identity development (Nasir, 2012). Findings focus on performances and moments of risk and vulnerability as resources for identity development of marginalized youth.