Nowadays, more-and-more aspects of our daily activities are digitalized. Data and assets in the cyber-space, both for individuals and organizations, must be safeguarded. Thus, the insurance sector must face the challenge of digital transformation in the 5G era with the right set of tools. In this paper, we present CyberSure - an insurance framework for information systems. CyberSure investigates the interplay between certification, risk management, and insurance of cyber processes. It promotes continuous monitoring as the new building block for cyber insurance in order to overcome the current obstacles of identifying in real-time contractual violations by the insured party and receiving early warning notifications prior the violation. Lightweight monitoring modules capture the status of the operating components and send data to the CyberSure backend system which performs the core decision making. Therefore, an insured system is certified dynamically, with the risk and insurance perspectives being evaluated at runtime as the system operation evolves. As new data become available, the risk management and the insurance policies are adjusted and fine-tuned. When an incident occurs, the insurance company possesses adequate information to assess the situation fast, estimate accurately the level of a potential loss, and decrease the required period for compensating the insured customer. The framework is applied in the ICT and healthcare domains, assessing the system of medium-size organizations. GDPR implications are also considered with the overall setting being effective and scalable.