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Selecting appropriate tutoring help actions that account for both a student’s content mastery and engagement level is essential for effective human tutors, indicating the critical need for these skills in autonomous tutors. In this work, we formulate the robot-student tutoring help action selection problem as the Assistive Tutor partially observable Markov decision process (AT-POMDP). We designed the AT-POMDP and derived its parameters based on data from a prior robot-student tutoring study. The policy that results from solving the ATPOMDP allows a robot tutor to decide upon the optimal tutoring help action to give a student, while maintaining a belief of the student’s mastery of the material and engagement with the task. This approach is validated through a between-subjects field study, which involved 4th grade students (n = 28) interacting with a social robot solving long division problems over five sessions. Students who received help from a robot using the AT-POMDP policy demonstrated significantly greater learning gains than students who received help from a robot with a fixed help action selection policy. Our results demonstrate that this robust computational framework can be used effectively to deliver diverse and personalized tutoring support over time for students.