Recently, Chile has experienced a significant increase in linguistically and culturally diverse immigrants from Haiti. However, little is known about how Chilean teachers cope with this issue. Using Haworth’s (2009) model of contextual layers of teachers’ work as a conceptual lens, this article reports the findings from two case studies. Findings show that participants often struggled to teach their culturally and linguistically diverse students. These difficulties were attributed to teachers’ low levels of professional preparedness to work with these students and limited in-school support. The article offers several implications for different stakeholders.