This project aims to provide insights into school dropout processes and post-dropout school-to-work transitions (STW) in Sweden and Finland, by taking advantage of the countries’ institutional similarities but different development over time. In the project, we conceptualize these processes and transitions through “social reproduction” theory and “career decision-making” theory, as influenced by a combination of factors at the micro, meso and macro level. To capture this complexity, the project will rest on a comparative design, and apply a mixed-methods approach using high-quality register-data in Sweden and Finland and semi-structured narrative interviews. Dropout processes and STW transitions are of major interest for both scholars and policy makers. However, most research currently comes from the USA. With this project, we seek to address this lacuna and contribute to knowledge that can help improve educational and labour market policies and youth wellbeing in the Baltic region. While Sweden and Finland are just two countries in the Baltic Sea region, the project will use its comparative design to test and refine theories with more general application and thus be beneficial to a wider array of countries. This makes the project relevant for both the interdisciplinary research community, and for policy makers in the Baltic Sea region and in Europe in general.