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