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Young children’s relationships with teachers predict social and academic success. This study examines contributions of child temperament (shyness, effortful control) and gender to teacher–child relationship quality both directly and indirectly through the frequency of teacher–child interactions in the classroom. Using an NICHD SECCYD sample of 819 first grade children, four findings emerged: (a) children’s shyness, effortful control, and gender contributed directly to teacher–child conflict and closeness; (b) children’s shyness contributed to the frequency of child-initiated teacher–child interactions, and children’s effortful control contributed to the frequency of teacher-initiated teacher–child interactions; (c) shyness related to teacher–child closeness indirectly through the frequency of child-initiated teacher–child interactions; (d) the frequency of child- and teacher-initiated interactions contributed to each other. Results inform practitioners and researchers of characteristics that put children at risk for failure to form positive relationships with teachers.