Despite extensive research on antecedents and consequences of counterproductive work behavior (CWB), factors contributing to it in educational settings and teachers have not been adequately addressed. With participants of secondary school teachers working in public schools (270), private schools (302), and other educational institutions (319) in Iran, this study explored factors associated with CWB at the individual (age, gender, and perceived justice), occupational (interpersonal conflicts and working hours), and organizational (job content, class size, and teaching context) levels. Significant relationships, with small effect sizes, were found between CWB and younger male teachers with low perceived justice. The results also indicated a linear trend with occupational variables and CWB in the public sector. An escalation in CWB engagement was observed with an increase in working hours and class size. There was a strong positive correlation between psychological demands and CWB, and negative associations were found for social support and decision latitude with significant differences in teacher categories. Hierarchal regression analysis confirmed the significant contributions of these variables to the variances in CWB. The implications have been discussed in light of study results by recommending policies and strategies to be used by school psychologists, administrators, and teacher educators to curtail dysfunctional behaviors and ultimately create school environments that promote teachers' job commitment and the delivery of high-quality education.