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The current study sought to determine the relationship between individual and contextual factors and teacher stress. Through analysis of the individual constructs of self-efficacy and personality combined with organizational justice, perceived supervisory support, and work-family conflict (WFC), one can evaluate how to effectively support teachers to negate the surmounting pressures of teachers. The study specifically looked at the interplay between the individual and contextual factors addressing all teacher experience levels and school settings to uncover possible sources of stress perceived as factors preventing attrition. Structural equation modeling (SEM) was used as the analytical framework to report the quantitative findings of composite scores for each construct.