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North American postsecondary students report: (a) feeling exhausted by academic work, and (b) experiencing levels of stress and anxiety compromising mental health, academic learning, and personal success (ACHA, 2016). Due to growing concerns about students’ mental health, this study examines how self-regulated learning processes and strategies during a semester relate to psychological well-being (PWB) and academic engagement. Undergraduate students (N = 118) enrolled in a learning-to-learn course completed 9 weekly online activities in which they: reflected on a challenge, described the strategy chosen to overcome that challenge, and completed a PWB measure and engagement measure. Findings include students who reported always achieving their goals also report higher overall PWB. Implications for theory, research, and practice are discussed.