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School leaders are central to recruiting, hiring, developing, and retaining teachers; however, we know less about how school leaders make sense of and navigate challenges related to this aspect of their work. We draw on interviews with school leaders from five U.S. school systems (rural, urban, suburban, Catholic, charter) to explore how school leaders frame and approach challenges related to teacher recruitment and retention. Using sensemaking theory, our research illustrates how school leaders interpret multiple priorities and requirements in designing their responses to staffing challenges while balancing instructional quality with teacher efficacy and satisfaction. This research has important implications for districts and principal preparation programs seeking to support school leaders in building and maintaining a high-quality, committed teaching staff.