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School administrators are often seen as the middle managers who are held accountable not only to their schools and communities but also to their employers. In order to successfully carry out their duties and responsibilities, school administrators must feel psychologically safe to speak up, ask a difficult question, voice an opinion, express a dissent, talk about a mistake, stand out for a position, or take a risk at work without fear of negative consequences. Psychologically precarious situations can compromise their ability to think, feel, speak, and act, and ultimately impact their leadership. This research provides insights into their psychological safety and associated barriers. Multiple logit regression models show school administrators felt less psychologically safe in their district than at their schools.