The Greek School Network (GSN) is a closed educational network that offers advanced telematic and networking services to all primary/secondary education schools and educational administration offices in Greece. The primary objective of GSN is to provide a network infrastructure for the interconnection of school PC laboratories so that modern educational methods and pedagogical models can be used in the school community securely and effectively. GSN has scaled in size, reached maturity, and is currently delivering a wide range of network and telematic services to students and educators. Being the second largest communications network nationwide, GSN is exposed to all kinds of security threats and, due to its educational hypostasis, naive user behaviour. The current paper presents an evaluation of security management solutions for the enforcement of policies, practices, and user protection methodologies proven viable within the GSN environment, as indicated by statistics and metrics on the use of the related services. The paper reaches the conclusion that GSN security services constitute a sound framework that can successfully cover the needs of the school community.