We report the results of a classroom study of three secondary mathematics teachers who had no prior experience teaching with technology as they began to use an online mathematics learning system in their lessons. We gave the teachers only basic instruction on how to operate the system and then observed them intensively over four school terms as they taught using it. We documented changes in the teachers’ Pedagogical Technology Knowledge and subsequently classified their various roles as technology bystanders, adopters, adaptors and innovators. Results show that all teachers made some progress toward using the system in more sophisticated ways, but the improvements were not uniform across the teachers. We suggest possible reasons to explain the variation and discuss some implications for teacher professional development.