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 Hawai'i'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 sociocultural pressure from their friends, parents, teachers, and America's growing presence in the islands while testing and exploring their own identities.