Although Finland still has a relatively low proportion of students with a migrant background, it has not been able to ensure that immigrants and their descendants have equal educational opportunities. Education could enhance integration but migrant backgrounds have a persistent impact. In this chapter, our focus is on post-comprehensive educational decision-making processes of immigrant origin adolescent girls, with the viewpoint of the multifaceted intertwinement of gender and ethnicity. We conceptualise the educational decisions as negotiations that adolescents have to have with their families, teachers, counsellors and peers. Within these negotiations, the negotiating parties try to push the adolescent to choose those educational paths they see valued and preferred, and away from the choices they see as unfitting or less valued. As the girls ‘negotiate their identities according to situational contexts’, their agency is constructed with ongoing and reflective negotiations with other people. In this chapter, we show how adolescent girls with an immigrant background in Finland face quite similar difficulties as ethnic minorities in other European and Nordic countries when continuing their education from compulsory education. We also illustrate with three ‘transitional stories’ the key challenges that girls with immigrant backgrounds encounter when making their educational decisions and integrating to education: structural boundaries, social boundaries and acculturation.