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This exploratory multiple case qualitative study was conducted to identify high-achieving undergraduate learners’ metacognitive regulatory strategies and self-regulatory-based decision-making for their learning within environments outside of the classroom. An online questionnaire, semi-structured interview, and a five-day diary using reflective assessment and momentary assessment daily prompts were used for data collection. Single-case analyses were conducted using qualitative content analysis while seeking themes across cases. Findings of the study prompts discussion and critique on critical aspects of communication towards, and among learners for further development of their self-regulatory behaviors and metacognitive regulation in independent educational settings. Metacognitive strategy imitation for academic success, and the critical stages of development of undergraduate learner’s metacognition thought to occur and continually advance into adulthood are discussed.