Although there are some success stories of technology integration in schools, it remains unclear in the literature how teachers become, and take on the identity of, exemplary users of technology in classrooms. Using concepts from cultural sociology, this article examines how an experienced elementary school teacher in Singapore, Cassie, accounted for her difficult learning journey and becoming an expert technology user. From interview data, we highlight the major milestones in Cassie's trajectory of learning and explain how structural factors at the policy, district and classroom levels afforded and constrained Cassie's learning and how she, in turn, slowly changed her pedagogy incorporating technology. We conclude by discussing issues of teacher learning and identity by way of contrasting against a more traditional view of teacher education and from the case example of Cassie, we further explicate the dialectics of teacher agents vis-a-vis the structure of teaching and education. (Contains 1 table and 1 note.)