The article focuses on the issue of using the modern testing system Kahoot! to achieve the goals of scaffolding in the developing digital environment and online education. It summarizes the results observed during the system-based practice, especially in the unprecedented situation of an abrupt and extensive shift from face-to-face training to a remote type of knowledge formation and assessment at the beginning of the COVID-19 pandemic. The article considers three types of tasks in an interactive testing system: from assessment ones to educational ones with extended functionality. Special emphasis has been placed on the active role of a student in personalizing his goal setting. The methodological approach proposed aims at consolidating the training capacity of the testing system: it contributes to the development of logical, critical, and creative thinking, stimulates high-order thinking, combines teamwork and competition. It maintains students’ motivation, their self-awareness as team contributors, and intensifies autonomous learning.