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This paper identifies the traits of educators working in an urban, nontraditional high school designed for students at risk of dropping out. Grounded in appreciative inquiry, the researcher utilized a qualitative, case-study design involving observation, active participation, and interviews. Data reveal traits that were both supportive and nonsupportive of helping students graduate. Supportive traits include expectation for graduation, flexibility, seeking small successes, engaging in reflective practice, pursuing collegial relationships, using identity markers to engage with students, and advocating for students’ well-being. Nonsupportive traits include deficit perspectives, apathy, and frustration with leadership. Finally, the paper discusses how school-level attention to students at risk of dropping out could be improved by building on educator traits that support moving students toward graduation.