The Italian labor market is recognized as disadvantaged for foreign-born citizens, with negative effects on their psychosocial wellbeing. In other countries, significant differences between career aspirations and expectations or perceived opportunities in native and foreign-born citizens has been welldocumented, mainly due to the presence of perceived socio-economic barriers, while studies on this topic are lacking in Italy. Addressing this research gap, we investigated the relationship between career expectations and aspirations in native and foreign-born citizens and the role of the perceived contextual barriers within an Italian sample. 291 inhabitants of Pioltello, a multicultural municipality in the metropolitan area of Milan, were involved in our quantitative study. Results suggest that, in line with the latest research trends, the Italian context differences already emerge in the aspirational phase, as foreign-born citizens are more aligned than natives with the labor market demands. Differently, natives operate a stronger realignment in the transition from career aspirations to expectations. Moreover, foreign-born citizens also perceive a stronger influence of socio-economic barriers on their career opportunities. Policy implications of this findings in psycho-social and educational fields, aimed at promoting individual and social wellbeing, are finally discussed.