A dedicated cyber risk assessment framework is essential for proactive risk mitigation. The chapter presents a framework that integrates machine learning techniques. It is a data-driven approach to quantitatively assessing cyber risks. In addition, various machine learning models—especially supervised machine learning—are presented. Overall, the chapter makes an innovative contribution to using machine learning to establish a robust and standard cyber risk management system that can be valuable for practitioners in different industries. Given cyber risk's complex, dynamic nature, it is necessary to go beyond typical risk management and technical approaches and incorporate various methods such as threat intelligence, vulnerability management, and incident response. Cyber resilience aims to consistently deliver the intended business outcome even in the face of unfavourable cyber incidents.