This study examined a random stratified sample (n = 62) of teachers' work across eight institutions on three tasks that utilized dynamic statistical software. We considered how teachers may utilize and develop their statistical knowledge and technological statistical knowledge when investigating a statistical task. We examined how teachers engaged in transnumerative activities with the aid of technology through representing data, using dynamic linking capabilities, and creating statistical measures and augmentations to graphs. Results indicate that while dynamic linking was not always evident in their work, many teachers took advantage of software tools to create enhanced representations through many transnumerative actions. The creation and use of such enhanced representations of data have implications for teacher education, software design, and focus for future studies.