Enhanced Course of Action (CoA) generation is a fundamental component of effective risk management and mitigation. This paper presents an extension of a system capable of integrating physics-based (hard) and people-generated (soft) data, for the purpose of achieving increased situational assessment and automatic CoA generation upon risk identification. The system's capabilities are enhanced through added support for managing multiple, concurrently unfolding risky events (situations) with the goal of attaining superior resource management and thus reducing the overall security operation costs. The CoA generation process is evaluated through a series of performance measures. The proposed conceptualization is validated via an elaborate experiment situated in the maritime world.