Drawing from our past research in middle school classrooms (Zepeda et al., 2015; Zepeda et al., 2019), this project aims to investigate the impact of supporting middle school students’ metacognitive skills during mathematics learning within the UpGrade/MATHia platform on middle school students’ metacognitive skills, mathematics knowledge, and motivation. In particular, we focus on supporting three metacognitive skills: planning, monitoring, and evaluating. Planning refers to identifying how to reach a goal, monitoring entails assessing one’s understanding and progress toward that goal, and evaluating refers to assessing the process of goal attainment. Although metacognition has shown to have many positive impacts on student learning and motivation, students rarely receive instruction on when, how, or why to apply these skills. This work aims to alleviate that void in their educational trajectories by leveraging the use of digital learning platforms.