This study examined a random stratified sample (n = 62) of prospective teachers' work across eight institutions on three tasks that utilized dynamic statistical software. The authors considered how teachers utilized their statistical knowledge and technological statistical knowledge to engage in cycles of investigation. This paper characterizes their problem solving and the ways they represented and explored data and discusses how teachers' work with representations seems to inform their problem solving. Recommendations are included for ways mathematics teacher educators can engage teachers in developing their knowledge for doing and teaching statistics with technology. (Contains 3 tables and 5 figures.)