Computer aided design (CAD) training and its aspects are described and analyzed in the paper. It looks at a traditional and technology-supported learning process aimed at analyses of teaching CAD and provision of knowledge assessment, as well as identification of problems in the CAD system training pro-cess. It was concluded that technology-supported learning process would con-tribute to solving these problems. An analysis allows set requirements for the intellectual tutoring system in the CAD system training. As the main problem in the use of CAD systems and in the assessment of learner’s results, there is an identifiable lack of information about the learner’s actions during execution of their tasks. Since an instructor issues an assignment, a student executes it and submits the result then the instructor acquires information about the results of the learner's work, but not the process itself. It is difficult (even impossible) for him to analyze the efficiency of the work performed – compliance of the tools/ func-tions used for the execution of the task, the sequence of the process, and its prac-ticability. Based on the study carried out, approaches for assessment of the use of computer-assisted design systems were offered for implementation within the framework of the study. The system created allows solving assessment problems of the use of CAD systems: an expert is being informed about activities of the learner during the execution of the tasks, the process of task completion.