Digital Game-Based Learning (DGBL) can be very effective. However, not all digital educational tools are equally effective in different learning situations, for learners of various backgrounds and various disciplines.The aim of the article is to compare the attractiveness, complexity and perceived usefulness of a gaming chatbot with puzzle tasks designed to teach programming with the same indicators of other educational tools.To conduct the study, a gaming chatbot with puzzle tasks, working in individual and team modes, a computer game, as well as a non-gaming chatbot for preparing for seminars and testing were developed and used in the process of teaching programming. The 1st year bachelor’s students of the educational program “Information Security” of the Faculty of Information Technology and Big Data Analysis at the Financial University under the Government of the Russian Federation used these digital educational tools and then evaluated their attractiveness, complexity, and usefulness.Several conclusions were drawn from the study. First, the use of game mechanics and the gaming chatbot with puzzles tasks significantly increases interest in the educational tool, so gaming chatbot has advantages over games and non-gaming chatbots. Second, the attractiveness evaluation of the gaming chatbot exceeded the corresponding evaluation of workshops. Both individual and team modes of gaming chatbot proved to be equally interesting, useful, and challenging for students. Consequently, the gaming chatbot can be used outside the classroom as well as in classroom activities. Third, if different types of gaming chatbot tasks, including those related to writing program code, are incorporated into the gaming chatbot, it will increase the usefulness of the chatbot.The results of the study contribute to the development of digital game-based learning using chatbots, particularly in teaching informatics and programming, and can help to increase the attractiveness of workshops and student engagement in general. The findings may be of practical interest to informatics and programming teachers.