This paper reports on a transition project where the Internet as a communication tool was used to facilitate interactions between primary school and high school students. The qualitative case study involved capturing the online interactions of the students and teachers as well as the use of questionnaires. Results of the study demonstrate that the use of the Internet allowed participants to engage in interactions that provided useful information to the primary school students as a way of preparing them for the transition to high school. There were a number of challenges identified in using the Internet to facilitate interactions which include identity and architectural challenges.