Aim/Purpose: The purpose of the current study is to explore positive and negative aspects of teacher-teacher communication via Facebook, as perceived by teachers in secondary education. Background: Teacher-student relationship is key to teachers' wellness and professional development and may contribute to positive classroom environment. In recent years, as social networking sites (e.g., Facebook) became popular, these connections have extended to such platforms. However, most studies of the use of social networking sites in the school context are pedagogically-driven, and research on the ways teacher-student relationship is facilitated by these platforms is meager. Methodology: We utilized a qualitative approach, analyzing responses to open-ended questions about this topic by middle- and high-school teachers' all across Israel (N=180). We used both top-down and bottom-up analyses. Contribution: This study contributes to the growing literature about the overall impact of using social networking sites on the educational milieu. Specifically, it contributes by shedding light on teachers' perspectives of that phenomenon. Insights from this study are important for educators and education policy makers. Findings: Overall, teachers who were connected to their students de facto, as well as teachers who expressed a wish to be connected to their students, acknowledged the advantages of befriending their students on Facebook, in terms of both teacher and student benefits. Teachers' overall viewpoint on the negative aspects of Facebook-connections with students is multifaceted. As such, our findings highlight the complexity of using social networking sites by teachers. Recommendations for Practitioners: We recommend that educators who wish to extend the relationship with their student to online platforms do so wisely, taking advantage of the benefits of using these platforms, and being aware of (and cautious about) potential drawbacks. We encourage educators to learn more about the potential uses of social networking sites and instant messaging services, and then to examine whether these uses may fit their educational agenda. We recommend that education policymakers make evidence-based decisions regarding the use of social networking sites by teachers and encourage school communities to discuss these issues together. Recommendations for Researchers: As technology develops rapidly, we recommend that researchers examine the topics raised in the current research with regards to other platforms, in order to better understand the technological aspects that may affect students' perceptions of the use of social networking sites and instant messaging services to communicate with their students. The issues studied here should also be studied in different cultural contexts. We recommend broadening the research and making results available to policymakers when making decisions regarding social media in educational contexts. Impact on Society: Understanding teachers' perspectives of their relationship with their students in today's digital, networked world gives us a better understanding of the changing role of teachers; hence, it may assist in planning teacher training and professional development, with the ultimate goal of realizing a better educational system. Future Research: Future studies should focus on other social networking sites and instant messaging services, as well as on other countries and cultures.