This article examines upper secondary vocational education students who have failed the exit examination (Matura) at least twice. Repeated failure leaves such students with only a basic education certification, restricting their access to higher education and limiting their labour market prospects. Although most of these young people wish to make another attempt to pass the Matura, they have lost their formal student status, along with its associated benefits, and most are compelled to seek employment. Academic failure, particularly at these critical transition points, can have profound implications on students’ educational and professional trajectories and their identities. The research question we posed here, therefore, is: How do the identities of upper secondary vocational education Matura examinees evolve during the two years after they fail the final examination? The data corpus for this study consists of biographical interviews with 46 informants who failed the Matura. The data analysis reveals that they struggled to anchor their identities through study, work, or family, with some exploiting non‐systemic permeability mechanisms.