Technology use in secondary mathematics courses has the potential to bring about broad changes in learning environment and teaching pedagogy, allowing students to communicate and collaborate in new ways and to conjecture, justify, and generalize findings. However, this potential is only realized when teachers use technology in ways encouraging these outcomes (Galbraith, 2006). The purpose of this study is to examine the integration of technology in secondary mathematics classrooms and to evaluate the effectiveness of its use in relation to students’ learning outcomes. This self study research was conducted in honors geometry and AP calculus classes. Data sources included transcripts of classroom discourse, student responses to both forced-response and open-ended surveys, and teacher journals. It was found that when students were the primary users of technology, they were more engaged in learning and higher attained higher levels of understanding, especially in relating different mathematical representations and generalizing patterns.