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The purpose of this study was to examine the influence of organizational constraints and principals’ authentic leadership on teachers’ psychological well-being. It was hypothesized that while organizational stressors would negatively influence, principals’ authentic leadership practices would pose positive influence on teachers’ well-being. Carol Ryff’s Psychological Well-Being Theory guided the study. Study employed non-experimental quantitative survey and causal comparative research designs. After the data screening procedures, the sample included 334 usable cases gathered from teacher participants. MANOVA and structural equation analyses were employed for the analyses of data. Findings supported the hypothesized relationships. More specifically, while organizational stressors negatively effected teachers’ well-being, principals’ authentic leadership positively effected their well-being. Conclusions drawn and implications for policy, practice, and research are discussed.