Software applications and reliable communication are key to offering regular and mission critical services online. To support a reliable, secure, and efficient offering of software services for critical infrastructures, cybersecurity and trustworthiness of software and computing infrastructures are vital. It is of utmost importance to take all possible measures to secure the computing systems supporting critical infrastructures and ensure uninterrupted availability of services. To secure these systems, our project proposes to design and develop a comprehensive and proactive data-driven vulnerability analysis framework. The proposed project, with its well-defined focus areas, is a cross-disciplinary effort within data science, machine learning, and cybersecurity with the purposes.