Automatic assessment is widespread in Mathematics, and it integrates computing environments and grading for the creation of meaningful and open-ended tasks for inquiring students’ understanding. This study focuses on three types of tasks related to univariate Calculus: explorative tasks, translation tasks, and example-generation tasks. They have been experimented with in two first-year university Mathematics modules in Italy and Sweden as group formative activities. The data consists of students’ responses to a survey that highlights their perception of the difficulty of the tasks and of the increase in understanding triggered by the activities. Our results show the difficulty perceived as reasonable and the increase as tangible.