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This paper examined whether school principals’ social and emotional learning (SEL) leadership positively influenced the degree to which teachers were comfortable addressing students’ SEL needs. In addition, we asked whether the frequency with which teachers collaborated positively moderated the relation we hypothesized between principals’ SEL leadership and teachers’ comfort with SEL instruction. We drew on data collected from 1,001 teachers in 25 schools in one of the largest school districts in a mid-western state. We adopted a latent moderated structural equation (LMS) approach to test our hypotheses. We found both that principal SEL leadership promoted teacher comfort with SEL instruction and, that this relation was positively moderated by the frequency with which teachers collaborated.