This paper takes an interest in migrant families' educational strategies in the upper-secondary school market in Stockholm. Based on interviews with parents and children in families living in a socially and economically disadvantaged neighbourhood, the analysis shows how conversion of symbolic and economic capital and assets between national-contexts and between generations shapes educational aspirations together with notions of pride, sacrifice, and guilt. What school choice alternatives that are considered viable options depends on the composition of assets and capital within the family, but also differs between family members depending on family dynamics and family members' different social investments in the neighbourhood of residence. The paper argues that migrant biographies are embedded in a gift economy that influences families' educational expectations. Moreover, parents and children identify sociospatial boundaries in the deregulated school market but develop divergent strategies to mitigate disadvantage.