This case study focuses on our efforts to engage students in one asynchronous, online undergraduate legal "pipeline" course, and the substantive revisions made to the course over 3 years to increase student engagement, self-reflection, self-regulation, and metacognition. A pipeline program is designed to identify, support, and guide students from diverse backgrounds to their graduate-level field of interest. We describe two strategic uses of a learning management system (LMS) to increase student engagement and self-regulated learning: a weekly reflection and engagement routine that was developed to address concerns regarding student-to-faculty engagement identified during the first version of the course, and a scaffolded multi-week skills-based activity that was developed to reinforce a critical course learning objective and help students monitor their own learning progress. During each iteration of the course, user data collected from the LMS and other integrated tools, along with student feedback and instructor and designer reflection on practice, informed substantive revisions to the learning activities described. Over three versions of the course, data suggest increased engagement, self- reflection, and self-regulation. We reflect on the implications of this work and possible applications to other settings.