Today, the world relies on complex infrastructures to host crucial services needed in a society. The need to keep a service running over time can be the key factor that keeps a person from dying. The worlds economy relies on complex IT-services to run, and businesses invest largely in new technology that can be used in large-scale infrastructures. System administrators are responsible for maintaining IT-services. When a service is up and running, the end-users can achieve maximal value from the application. The value indicates the need for the IT-service for an end-user. When a IT-service stops working it could be a costly affair for businesses to get the system up and running. Educational IT focuses mainly on teaching students methodologies and principles of IT. Students gain knowledge into how to create and build new systems from scratch. The knowledge of evaluating a running infrastructure is today something one must learn from experience. This thesis aims to build a framework that can be used by teachers to evaluate student-progression in system administration-related courses. The students will benefit from the solution by getting continuous feedback on their progress in courses. The feedback aims to give students a better insight into evaluating IT-infrastructures, and to map potential vulnerabilities that may cause future problems. The prototype developed reflects the model designed, and aims to simplify the process of automating assessments between teacher and student. The prototype consists of an application along with a larger infrastructure. The thesis is written as part of a master-program in Network and System Administration, and focuses on the operational aspect of evaluating IT-services.