The transition from school to the labour market is a significant milestone in every person's life, marking the path to adulthood, career, and independence. However, this transition may pose challenges for youth, leading them to unemployment. Such experiences not only create economic imbalances in labour markets and increase social tension but also have long-lasting effects on individual well-being. Despite ongoing EU and global efforts, such as the 2020 Recommendation on Bridge to Jobs and SDGs 4 and 8, many young people face difficulties in securing stable employment, especially endangered is youth with vocational qualifications. Existing policies, addressing economic indicators of labour markets, often leave unaddressed real experiences of youth and how national systems of school-to-work transition (STWT) shape these experiences. The project “School-to-Work Transition of Youth with Vocational Qualifications: Cases of Germany and Italy” (TWISTY) addresses these gaps by focusing on biographies of young people navigating or finishing their transitions to stable employment. The project’s novelty lies in contrasting these experiences with policy narratives, identifying mismatches and disclosing overlooked factors in current practices. It focuses on Germany and Italy because despite political, social and economic similarities, they demonstrate astonishing differences in youth unemployment and organisation of STWT systems. Through the policy analysis and study of individual experiences, TWISTY will offer bottom-up solutions to improve STWT strategies. The findings will not only fill in the gaps in understanding of personal trajectories of skilled youth to stable employment in complicated STWT systems but also inform more nuanced policy recommendations that can be adapted to other contexts with similar socio-economic conditions. The project aligns with the EU policies on integrating young people into the labour market and contributes to the achievement of SDGs.