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This study aimed to examine post-secondary students’ deployment of strategies in response to challenges encountered during independent studying. We used experience sampling method with a daily study diary, in which undergraduate students planned study sessions over two weeks in the academic semester. Students reported (a) the main challenge encountered, (b) the strategy deployed to address that challenge, and (c) the strategy effectiveness. Overall, students most frequently reported (a) challenges related to: Initiating and sustaining engagement (23.6%), Cognitive engagement (21.5%), and Motivation (21.4%), and (b) strategies involving Social and Environmental Structuring (21%), and Effort Management (20.90%). An important contribution of this study is that it reveals the perceived effectiveness and frequency of strategies for specific types of challenges encountered during studying.