As technology becomes increasingly integrated into education, ensuring robust cybersecurity practices in schools is essential. This paper examines the “Digitally Safer School” initiative in Estonia, which aims to enhance cybersecurity awareness and practices among students, teachers, and the broader school community. Using a mixed-methods approach, the study evaluates the current state of cybersecurity in schools, identifying strengths, weaknesses, and opportunities for improvement. Key findings highlight gaps in documentation, staff training, and the integration of cybersecurity into curricula, alongside strengths in technology accessibility and IT support. The study introduces a maturity model and self-assessment tool that schools can use to measure and enhance their cybersecurity readiness. Schools are encouraged to foster a culture of digital safety through staff training, student engagement, and community involvement, supported by secure IT infrastructure and effective incident management protocols. The findings demonstrate that significant challenges remain while schools have progressed in some areas. The “Digitally Safer School” initiative offers a scalable framework for improving cybersecurity education and practices, serving as a model for global adoption in educational settings. This paper's results support the claim that we still need to push for collaboration between policymakers, educators, and communities to create resilient, digitally secure learning environments.