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This study strengthens the empirical evidence for the importance of teachers’ cognitive flexibility on student engagement – defined as deep, complex, and adaptive knowledge for how to effectively use culturally responsive-sustaining teaching to engage diverse students. We present a new instrument for measuring teachers’ cognitive flexibility on engagement. We then draw on teacher assessment and interview data, along with student survey data, to illustrate how the instrument assesses teachers’ cognitive flexibility on engagement and the strength of that knowledge for supporting student engagement in middle school classrooms. We show that teachers who demonstrate more complex thinking about student engagement tend to be those in whose classes students report higher levels of engagement.