In recent years, educational systems in Europe have experienced a rise in the number of immigrant youth. The experiences of immigrant youth facing the challenges of an unfamiliar educational system is of continuous relevance in youth studies. This article aims to explore the schooling experiences of 19 immigrant youth in Sweden, focusing on the institutional obstacles they encounter as students in the national educational system. It draws on semistructured interviews with immigrant youth attending upper secondary school or preparing for it by taking transitional classes. Findings are that familiarity with the majority culture, how the educational system works and how to use the majority language for learning purposes in Sweden constitute crucial knowledge for progress in upper secondary education. However, immigrant students state they have not been adequately prepared for these demands in their transitional classes. The authors suggest acknowledging students' cultural backgrounds and argue for allowing English parallel to Swedish as a transnational language of communication during a transition period, thereby improving students' chances of having their embodied cultural capital validated in the upper secondary school system.