In this paper we describe a methodology for designing and evaluating lab assignments based on the fulfilment of milestones. The approach relies on the integration of ICTs with an automatic, milestone-based evaluation. The final goal of this methodology is to diminish educators’ workload on lab assignments, so they can focus on the development of the assigned tasks, and to enhance students’ experience by providing direct and real-time feedback on their progress. This approach encourages autonomous learning on the students and optimizes the time invested by the educators during the lab assignments. In order to validate our proposal we have applied this methodology in several courses related to Information Security. The results of this experience show that the methodology improves students’ performance, while facilitating the work of the educator.