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The collection and use of student data in higher education institutions have increased in recent years with the widespread adoption of learning management systems (LMSs). These large-scale data have the potential to provide scholarly and practical insights about student learning and how their learning evolves over time. We used a learning analytics approach on an institutional dataset to cluster students (N=2293) based on behavioral characteristics, such as engagement and self-regulated learning (SRL), and observed how these clustering patterns changed over time and influenced academic performance and student retention. Our results highlight the importance of long-term SRL behaviors for academic success and demonstrate that SRL behaviors can act as early predictors of at-risk students.