This study describes the results of a study which compared the educational and identity experiences of teenage students of Haitian origin in Montreal who belonged to the first or second immigrant generation. Half of the students, who had recently immigrated, were born in Haiti and had completed their first years of schooling there. The others, whose parents were immigrants, were born and raised in Quebec. By studying these two groups of youths it is possible to examine the similarities and differences in their adaptation to the school system as well as their cultural identity regarding their home country and country of residence. Compared to their peers who were born and socialized in Quebec, do the adolescents born in Haiti turn more towards their culture of origin and feel less close to the receiving community? Individual and group interviews revealed that the youths from both generations who participated in the study are very concerned about obstacles linked to their race and their status as immigrants. Most of the time, they manage to combine values from both Haitian and Quebec cultures in constructing their self-identities. Nonetheless, they feel a certain distance from the majority group, who is perceived as being responsible for the stigmatized collective image of their community. Finally, this study leads to a better understanding of the social interactions of teenagers of Haitian origin within the school and the challenges arising from identity development in a multicultural environment.