We examine the effects of school context on educational outlooks and outcomes of the children of immigrants, in comparison with natives in Spain, an under-represented case in the international literature and a fast growing immigration destination in Europe. Using two sources of hierarchical data, 2011 Chances Survey and the 2010 Secondary Schooling National Evaluation Survey, which cluster students across schools, we investigate the factors that contribute to the formation of long term educational careers. To start with we analyze performance from both an objective (test scores in mathematics) and subjective perspective (estimation by children and also their parents of whether individual school results will allow them to proceed to tertiary education). Then we turn our attention to the adjusted educational expectations (controlled for prior performance) of children. Our results reveal the different way that school context works for immigrant and native origin children. Our multilevel regression analysis finds significantly worse school results among immigrants (test scores). Although immigrant children themselves understand the constraints that such disadvantage imposes on their future educational careers, immigrant parents seem to hold on to a rather unrealistic position. This parental optimism in turn seems to boost the career expectation of immigrant children independent of school effects. Thus while school context determines the performance of immigrant origin students to a greater extent than those of natives, the opposite is true for expectations. The formation of aspirations is more family-oriented among immigrants, and thus more positive, than among natives