The exit examination from upper-secondary school represents an essential part of the educational trajectory. However, the transition to the labour market or higher education can be complicated by failure. The qualitative study deals with repeatedly unsuccessful students who have struggled to pass the Czech exit exam called the Matura examination. The research focused on how students approach exam attempts in terms of preparation and their reflection on the impact of failing. The study uses the self-regulated learning model to understand these aspects. The data used in this study consisted of 44 biographical narrative interviews with 27 informants aged 18 to 21 years, followed two years after their first attempt at the exit examination. Results show that students adopt ineffective learning and motivational strategies during the preparation phase before the exam. However, after the second attempt failure, which is associated with social pressure and negative emotions such as shame, they tend to change the way of preparation.