This article explores the meaning and significance of disobedience and independent behavior among students at an important school in early colonial Senegal: the School for Sons of Chiefs and Interpreters, which was established to train future generations of loyal African auxiliaries. Relying on descriptions of student behavior in letters or reports from school personnel and on letters from students themselves, it considers student activities like destroying or losing their school-issued clothing, staying out past curfew, and establishing social ties with the school’s African employees. The article makes the case that these actions help us understand how Africans, colonial officials, and others negotiated colonial schooling—and indeed, colonial rule—through the mundane and the quotidian. As students reacted to school uniforms and nurtured social relationships with other Africans, they not only pushed against regulations in the school, but they also suggested that colonial authority—even in the colonial capital—was not as complete as the French liked to think.