The purpose of this article is to describe some educational contexts and challenges experienced by students and educators who live in Nunavut. The data for this qualitative study include twenty-four semi-structured interviews involving fourteen principals, vice-principals, and teachers from Nunavut. Four themes surfaced: student attendance, legacy of residential schools, lack of Inuktitut/Inuinnaqtun resources, and transient teachers. With regard to student attendance, participants viewed this issue as one of the most challenging aspects of their education system. Second, participants emphasized that the Nunavut Department of Education was promoting fluent Inuktitut/Inuinnaqtun and English learners. While participants valued the importance of maintaining the vitality of the Inuit language, they believed resources to promote the Inuit language were limited. Third, many principals indicated that the legacy of residential schools was a reason some school-parent relationships lacked an element of trust. Last, participants explained that the constant teacher turnover caused relational strains between educators, students, parents, and community members. Cultural compatibility theory was employed as the philosophical basis to conceptualize findings. This theory assumes that a student needs an educational experience where that learner can see, feel, hear, taste, and touch his/her cultural values and beliefs. The design of educational programs need to foster the unique identities of Inuit peoples through the implementation of curricula built upon local Inuit culture, language, and knowledge. In doing so, attendance issues within school can be addressed, for example. Also, when parents see their culture within the school curriculum and environment, they will feel more welcomed and at home in this familiar context.