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Relying on the contingency model theory, the current study examines the moderating role of school attributes and principal-teacher gender similarity on the relationship between Principal System Thinking (PST) and the teacher withdrawal behaviors of absenteeism and intent to leave. Data were collected from 220 participants in Israel: principals, school management team members, and teachers. Results from hierarchical regression analyses showed that with principal-teacher gender dissimilarity, teacher absenteeism was low with high PST. The results also showed that with high bureaucratic school structure, teacher absenteeism was lower with a low level of PST. Finally, with high bureaucratic school structure, teachers' intent to leave was higher with high PST. Implications for theory and practice are discussed.