How teachers think about student thinking informs the ways in which teachers teach. By examining teachers’ anticipation of student thinking we can begin to unpack the assumptions teachers make about teaching and learning. Using a “mathematics for teaching” framework, this research examines and compares the sorts of assumptions teachers make in relation to “student content knowledge” versus actual “learning paths” taken by students. Groups of teachers, who have advanced degrees in mathematics, education, and mathematics education, and tenth grade students engaged in a common mathematical task. Teachers were asked to model, in their completion of the task, possible learning paths students might take. Our findings suggest that teachers, in general, had difficulty anticipating student learning paths. Furthermore, this difficulty might be attributed to their significant “specialized content knowledge” of mathematics. We propose, through this work, that examining student learning paths may be a fruitful locus of inquiry for developing both pre-service and in-service teachers’ knowledge about mathematics for teaching.

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