The goal of this work was to determine whether contextualized prompting can promote student engagement with resources designed to develop self-management skills. In a second-year social and developmental psychology unit, a special section of the learning management system (LMS) contained multiple self-management tools/resources which covered topics such as time-management, study strategies, and emotional regulation. "Just-in-time" (JIT) prompts regarding selected self-management tools were delivered through LMS reminders (e.g., time-management tools early in the term). The primary measures were the number of hits on each resource and the percentage of students who accessed each resource, which allowed comparison between those resources selected for JIT LMS prompts, and those that were not. Across two studies (whereby in the second study, the LMS section was simplified, and the frequency of JIT prompts was increased), it was found that there were more hits on the JIT-prompted resources than those resources that were not prompted, and that the percentage of students accessing the JIT resources generally dropped off across the term. In addition, Study 2 suggested that increasing the frequency of JIT prompts did not increase student engagement. Limitations, implications, and future directions for this initiative are discussed.