Accompanying the achievement gap across racial and ethnic groups is a disturbing gap in discipline referrals. For the past thirty years, evidence shows that African American adolescents have been over-represented in school suspensions. Discipline reports across the nation also indicate that disciplinary action for defiance is a common reason for exclusion from class. Yet research is lacking on perceived defiance in the high school classroom and its contribution to the over-representation of African American students in referrals. Two studies at a large, urban high school were conducted to examine student beliefs and teacher qualities that help explain the classroom-dependent nature of defiance and the sanctioning of African American students. Study 1 used an epidemiological review of one year of discipline data and the population of 442 students referred for defiance. Study 2 used repeated measures analyses and multilevel modeling with a sub-sample of 33 defiance-referred students and two of their teachers. The studies found that defiance was the most common reason for African Americans' referrals. It documented that the majority of students were referred by one teacher, suggesting situationally specific patterns of referral. Attendance records, classroom grades, and teacher reports showed that students behaved more defiantly and less cooperatively with teachers perceived by students as unfair and untrustworthy in their use of authority. The same students behaved less defiantly and more cooperatively with teachers perceived by students as fair and trustworthy in their use of authority. Predictors of student trust and obligation to teacher authority included teacher caring and high expectations for behavior, providing evidence for the importance of an authoritative teaching style for fewer problems with discipline. These findings imply that to narrow the discipline gap, schools should focus on strengthening teacher relationships that are responsive to African American adolescents and demand the best from them. Evidence that student defiance is context specific may be helpful in challenging the labeling of African American students and focus attention on the contextual contributors to the behavior.