This article explores the efforts of Native Hawaiian students to appropriate and take control of their schooling as part of a broad indigenous story of empowerment during Hawaiʻi’s territorial years (1900-1959). Histories of this era lack a visible indigenous presence and contribute to the myth that Natives passively accepted the Americanization of the islands. This article challenges this myth by examining Native student writings to tell a story of Native involvement in education as a pragmatic strategy designed to advance distinctly indigenous interests through the American education system. These stories reveal schools as complex sites of negotiation where Native students regularly navigated socio-cultural pressure from their friends, parents, teachers, and America’s growing presence in the islands while testing and exploring their own identities.