Recognition of the disproportionately high failure rate of American Indian students in local public schools caused Tribal officials to consider development of a reservation-based charter high school. Eagle High School opened its doors August 30, 2004. This article presents the findings of a two-year study, which examined the struggles of the school staff as they sought to provide a culturally rich environment and curriculum that would engage and challenge students academically. Cummins' (1992) theory of cultural differences provides a schema for discussion of the findings. Analysis of the issues raised by the study foregrounds the complexity of factors affecting both the development of a culturally grounded charter school and the achievement of students attending the school.