In this paper, we examine the development of pre-service mathematics teachers’ use of multiple representations during teaching in technology-rich environments. The pre-service teachers took part in a preparation program aimed at integration of technology into teaching mathematics. The program was designed on the basis of Technological Pedagogical Content Knowledge (TPCK) framework; and the mathematical content chosen for the program was the concept of derivative. The pre-service teachers’ development was scrutinized in terms of their knowledge of representations, of connections established among the representations, and of the aspects of derivative emphasized by these connections. On the basis of our analyses we argue that any attempt to prepare pre-service teachers for effective use of technology in teaching mathematics needs to explicitly focus on the functions of multiple representations in tandem with the mathematical content under consideration. We discuss the educational implications of the study in designing and conducting of the preparation programs related to the successful integration of technology in teaching mathematics.