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This qualitative study investigated organizational mindfulness in rural secondary schools in Tennessee. This study sought to understand how principals in this context understand the practice of mindfulness and what motivated them to practice it. This investigation is based on Hoy, Gage, and Tarter’s (2004) theoretical construct of school mindfulness: focus on failure, reluctance to simplify, sensitivity to teaching and learning, commitment to resilience, and deference to expertise. Six rural secondary school principals (three high-performing and three low-performing) participated in the study and were matched according to school size and socioeconomic (SES) percentages. Qualitative analysis found the following emergent themes: situational awareness, social-emotional learning, and care. Findings from this investigation suggest avenues for future research and implications for administrative training programs.