This paper focuses on the support given by schools to students who are likely to leave Swedish compulsory education without the grades required to enter upper secondary education (USE). The aim is to increase knowledge about career counselors’ and teachers’ strategies and work in lower secondary schools in order to facilitate this critical transition, and to examine factors influencing this support. It takes as its starting point theoretical frameworks stressing the agency of professionals in welfare organizations, and the importance of support during the educational transitions of young people at risk. The paper builds on interviews with 20 teachers and career counselors in six municipalities of varying character. Teachers’ and career counselors’ micro-choices have a major impact on the support provided to students. Their work consists of direct and indirect support, with the former referring to prescribed professional assignments. Indirect support, taking the form of advocacy, relational, and emotional work, is not officially recognized, but appears to be a necessary precondition for the direct support. The transition seems to be at risk of becoming overly fragile unless the support is characterized by sustained collaboration between school actors in compulsory school, and between compulsory and USE levels.