The following study describes design research in an elementary school near the metropolitan D.C. area with a diverse student population. The goal of the project was to design tasks that leveraged technology and enhance the access to critical thinking in specific mathematical concepts: data analysis and probability. It highlights the opportunities that technology-rich mathematics environments afford the teachers and the students in their ability to teach and learn through critical thinking. In addition, the article illustrates how to design and implement mathematical tasks using technology to give opportunities for higher mathematical thinking processes as defined by the National Council of Teachers of Mathematics (NCTM, 2000): problem solving, connections, representations, communication, reasoning and proof. (Contains 4 figures.)