This paper investigates the well-being of adolescent migrants compared to their native counterparts during the status transition at the end of lower secondary school in England, Germany, the Netherlands and Sweden. We use data from wave 1 and 3 of the CILS4EU-Project (Children of Immigrants Longitudinal Survey in Four European Countries) and analyze well-being (life satisfaction and problem behavior) as a function of the welfare systems, their institutionalized educational trajectories and the cultural distance between the country of origin and the host society. We find that during the transition, the well-being of all students increased in those countries where well-being scored lowest (England and Germany) and decreased where it scored highest (the Netherlands and Sweden) in advance. The greater the distance to the culture of the host society was, the stronger the decrease in well-being was. Interestingly, while the well-being of native students decreased with upward track mobility, it increased for culturally distant students (vice versa effects are shown for downward track mobility). This result remained stable even after controlling for personal characteristics.