This paper intends to show that conflict emerging from multiple and competing perspectives on social reality, may not necessarily be avoided in class, but it could instead become the starting point of critical discussions among teachers and students. To this end, the paper focuses on the exploitation of essays written by immigrant students attending Greek Lyceums (15–18 years old) to promote conflict-dialogue processes in class, which are most compatible with critical literacy. It suggests that language teaching concentrating on texts including immigrant experiences and ambivalent identities constructed by immigrant students, could underline the conflict between majority expectations or pressures and minority efforts to adjust to a complex, often inhospitable context. Such a conflict could enhance immigrant and non-immigrant students’ critical literacy by bringing to the surface and critically discussing assimilationist and monoculturalist ideologies, thus promoting a culturally sustaining pedagogy.