KERMIT is an intelligent tutoring system that teaches conceptual database design using the Entity-Relationship data model. Database design is an open-ended task: although there is an outcome defined in abstract terms, there is no procedure to use to find that outcome. So far, constraint based modelling has been used in a tutor that teaches a database language (SQL-Tutor) and a system that teaches punctuation and capitalisation rules (CAPIT). Both systems have proved to be extremely effective in evaluations performed in real classrooms. In this paper, we present experiences in using CBM in an open-ended domain. We describe system’s architecture and functionality. KERMIT has also been evaluated in the context of genuine teaching activities. We present the results of an evaluation study with students taking a database course, which show that KERMIT is an effective system. The students enjoyed the system’s adaptability and found it a valuable asset to their learning.