We evaluated the impact of a set of interventions to repair students' disengagement while solving geometry problems in a tutoring system. We present a deep analysis of how a tutor can remediate a student's disengagement and motivation with self-monitoring feedback. The analysis consists of a between-subjects analyses on students learning and on students' attitudes towards mathematics and perceptions of the software, and a deeper analysis on students' engagement within the tutor. Results show that the general trend over time is for students to become more disengaged while using a tutor, yet students can be coaxed into reengagement after viewing interventions that promote self-reflection and self-monitoring –a simple open-learner model accompanied by suggestions and encouragement.