Cyber Observer is a holistic cyber-security management and awareness solution. It continuously measures cyber-security status by retrieving and analyzing critical security controls from security relevant tools. The technology indicates misconfigured, malfunctioning, or lacking cyber-security tools; security gaps and recommendations for improvement; and continuous analytics and alerts on deviations from normal behavior. Cyber Observer provides users with a unified dashboard of their entire cyber-security ecosystem, enabling them to easily identify weaknesses, reduce mean time-to-detect, prevent breaches, and advance organizational cyber-security posture and maturity.