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This study explores the effects of a principal’s interactions with teachers and the effect on teacher well-being. Due to the predictive nature well-being has on a teacher’s personal and work life, including health, productivity, job absenteeism, and engagement (Beck & Harter, 2014; Rath & Harter, 2010; Sears et al., 2014), the understanding of how principals can positively impact teacher well-being is the primary goal of this study. The interactions between the principal and teacher were studied in three categories: interaction frequency, interaction quality, and combined interaction frequency and quality levels. A hierarchical multiple regression and estimated marginal means analysis were used to find the relationship of an interaction frequency composite, interaction quality composite, and the combined composites with teacher well-being.