The paper is devoted to the concept map-based intelligent assessment system that promotes students’ knowledge self-assessment and supports teachers in improvement of study courses through systematic assessment and analysis of students’ knowledge on the basis of concept maps. During the last five years, both the system’s functionality and knowledge assessment approach were improved persistently, and at the moment, certain level of maturity is reached in both directions. The paper focuses on general principles of functioning of the last prototype, tasks provided, teachers’ and students’ support, scoring and adaptation mechanisms. At the end of the paper, retrospection of the system’s evolution and evaluation results is provided.