The relationship between student brinkmanship, defined as an assertive student behavior which attempts to challenge school authority while avoiding negative sanctions, and classroom social structure in five secondary school classrooms was investigated through a field study. Subjects were 185 students in a small rural high school in Georgia. Participant observers for the study were the researcher, the school's principal, and the school's reading supervisor, who observed six classes rated as either relatively low or high in robustness, i.e., interesting, challenging, and meaningful. Rated as low robustness or routinized classes were a ninth-grade history class, an eleventh-grade English class, and a beginning typing class, while the high robustness classes were a twelfth-grade physics class, a ninth-grade physical education class, and an eithth-grade English class. Results indicated that: (1) positive rapport between students and teacher, low levels of routinization, and moderate to high levels of teacher legitimacy led to infrequent student brinkmanship; (2) low rapport and teacher legitimacy reduced class effectiveness and efficiency and led to student hostility and institutional sabotage; and (3) low rapport between students and teachers, low teacher legitimacy and low degrees of routinization led to all forms of student brinkmanship. (HLM)