This study examined the joint relationship between teachers' perceptions of principal's and immediate supervisor's empowering behavior in predicting the four dimensions of teachers' psychological empowerment, in terms of teachers' sense of meaning competence, autonomy, and impact. Three hundred four teachers in Singapore participated in this study. Results from moderated path analysis and simple slope tests indicated the presence of an interactive relationship between teachers' perceptions of principal's and immediate supervisor's empowering behaviors in predicting teachers' sense of meaning, competence and autonomy, but not impact. Further analysis indicated different types of moderating mechanisms underscored their interactive relationship (i.e. enhancing or substituting mechanisms). Teachers' perceptions of principal's empowering behaviors added more unique variance to teachers' perceptions of immediate supervisor's empowering behaviors in predicting teachers' sense of impact. This study highlighted the dynamic interplay of school leaders' empowering behaviors and teachers' psychological empowerment dimensions and it therefore has important implications for both school leadership and teacher developments.