| Sumario: | Background: The development and distribution of digital learning software, such as intelligent tutoring systems (ITSs), has evolved into a billion‐dollar industry, impacting a vast number of students worldwide. A large number of studies on ITSs have focused on their effects on learning outcomes. However, less is known about student engagement and dropout when ITSs are used in real classroom settings over extended periods, particularly with regard to how these patterns may be linked to different assignment scenarios within ITSs. Objective: The present study aimed to explore whether student engagement and dropout varied based on whether mathematics problems within the ITS were assigned by teachers or self‐assigned by students. Methods: We evaluated rich data from an ITS for learning mathematics used in Germany and the Netherlands (~139,000,000 problems; n ~ 194,000 students) between 2016 and 2023. To examine whether students' engagement and dropout, both within and between students, varied based on the two assignment scenarios (teacher assigned vs. self‐assigned problems), we employed regression and survival analyses. Results and Conclusions: Our results revealed that, in both Germany and the Netherlands, students with teacher‐assigned problems consistently (i) dropped out later, (ii) were active for significantly more weeks and (iii) worked through more mathematics problems each week than those who self‐assigned problems. The results were robust across academic school years in the examined period. Overall, our study raises questions about the use of digital learning software as a stand‐alone solution and suggests embedding such software in real‐life learning scenarios involving teachers. Lay Summary: What is currently known about this topic? ○Digital tools like intelligent tutoring systems (ITSs) have been developed to support student learning.○Despite large investments, real‐world use of ITSs is not yet fully understood.○Student dropout and disengagement limit the benefits of digital tools.○There is a need to better understand factors linked to dropout and engagement.What does this paper add? ○We examine links between assignment scenarios in ITSs and student engagement/dropout using data from real classroom settings.○Students drop out earlier and engage less when they self‐assign problems in the ITS than when teachers assign problems to them.○We show that these effects appear in both Germany and the Netherlands.Implications for practice and/or policy ○Teachers may need to stay involved when students use ITSs over extended periods.○ITSs may be better integrated into classroom practices rather than used in isolation.○Involving educators in the design of ITSs may help align these tools with classroom realities.
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