Since the management of technology has become central to the operations of organizations worldwide, digital assets have also emerged as critical weak points, making it essential for companies to assess cyber threat levels to prevent security breaches and meet requirements from insurers and regulatory bodies. The evaluation of cyber risks, however, is time-consuming, resource-intensive, and requires skilled personnel, comprehensive data gathering and rigorous analysis. Building upon RiskMan, an expert system for automatic assessment of organization cyber-risk, based on open-source tools and publicly available data, this thesis aims to expand the framework through the evaluation and subsequent integration of additional tools, enhancing the process through the use of AI.