The introduction of the Internet at schools has raised new pedagogical challenges facing educators trying to ensure children's awareness of the possible dangers when surfing the Web. This article aims to investigate how teachers evaluate the possible dangers that students might face when surfing the Net for various educational or interpersonal purposes, and the teachers' technological skills in terms of their ability to promote Internet safety awareness when supervising elementary students surfing the Web within the school premises. Using questionnaire surveys from 179 teachers in Greece, the present data showed that teachers who tended to incorporate technology in their every-day personal or professional habits were found to be more effective in promoting Internet safety issues in class such as discussions with students or teaching children moral behaviours when navigating the Net than their less technology enthusiastic colleagues. The current work strongly recommends the importance of a more systematic promotion of Internet safety awareness in primary schools as most Greek teachers seem to luck the basic pedagogical skills for exploring Cyberspace alongside their students, and giving worldly guidance and wisdom screen-by-screen. (Contains 5 tables and 3 figures.)