The use of instructional technology in secondary mathematics education has proliferated in the last decade, and students' mathematical thinking and reasoning has received more attention during this time as well. However, few studies have investigated the role of instructional technology in supporting students' mathematical thinking. In this study, the implementation of 63 mathematical tasks was documented in three secondary and one middle school mathematics classroom, and the Mathematical Tasks Framework (Stein & Smith, 1998) was used to correlate the cognitive demand of mathematical tasks with the use of technology as an amplifier or reorganizer of students' mental activity (Pea, 1985, 1987). Results indicate that the use of technology generally aligned with teachers' current practice in terms of the distribution of low- and high-level tasks enacted in their classrooms. However, the use of technology as a reorganizer of students' thinking was strongly correlated with these teachers' attempts to engage their students with high-level tasks. The distinction between using technology as an amplifier or a reorganizer is refined and extended through its application at the grain size of mathematical tasks, and implications for mathematics teacher education are discussed.