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Undergraduates’ first-year experience in engineering education impacts their retention and persistence. Strategic learning strategies (i.e., skill, will, and self-regulation) are important to students’ academic achievement and retention. This study examined how skill mediates the relationship between self-regulation and will, and how the constructivist learning environment influences students’ self-regulation. Data were collected from 293 engineering undergraduates, using Constructivist Practices in the Learning Environment (CPLE) and Learning and Study Strategies Inventory (LASSI). The results indicated skill mediated the relationship between self-regulation and will, and one dimension of the constructivist learning environment (i.e., sharing ideas with others) was correlated with self-regulation. This study helps faculty and researchers see how to use strategic learning strategies as they encourage engineering students toward academic success.