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Research shows that course-based interventions can enhance college students' indicators of self-regulated learning (SRL) and academic success. Such interventions during summer or less traditional semesters, however, are largely unexplored. We examined an online SRL learning-to-learn course across five summer semesters to evaluate its effectiveness in promoting students' SRL behaviors and well-being. We also considered the role of first-generation status and academic level. Results indicate that several adaptive indicators of SRL and well-being improved, whereas some maladaptive behaviors (i.e., procrastination, disengagement, academic burnout) did not. First-generation students also experienced greater procrastination compared to continuing-generation students. Our results support the effectiveness of SRL interventions; however, the results suggest that challenges unique to summer terms may require more targeted academic support.