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It is widely agreed that schools today must push beyond the basics and engage all students in "deeper learning." This paper reports results from a four year ethnographic study of 30 high schools seeking to achieve ambitious instruction. This paper offers a theory of deeper learning by looking across these 30 schools for elements that are similar in the deepest classrooms. It also identifies school-level mechanisms that differentiate those who succeed at developing deeper learning from those who aspire but fail. Implications suggest that deeper learning is powerful but rare, and that we will need to rethink core elements of the grammar of schooling if deeper learning is going to become a widespread reality.