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An intuitive goal for principals is to hire the best teachers. Indeed, researchers suggest hiring is a key component to improving schools. While a growing body of work explores principal hiring processes, less research explores principals’ hiring decisions in school contexts where teacher shortages constrain principals’ ability to hire the best candidates and maintain stable work environments that promote teacher retention. Using a qualitative case study design, this study focuses on principals’ hiring and school organizational practices in a context where acute levels of teacher shortages exists. Findings from this study advance existing frameworks for school leaders hiring practices by extending our understanding of principals’ strategic behaviors.