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Learning exercises that activate students’ additional cognitive understanding of course concepts facilitate contextualizing the content knowledge and developing higher-order thinking and problem-solving skills. Student-generated instructional materials such as course summaries and problem sets are amongst the instructional strategies that reflect active learning and constructivist philosophy. The contributions of this work are twofold: 1) We introduce a practical implementation of inside-outside learning strategy in an undergraduate deep learning course and will share our experiences in incorporating student-generated instructional materials learning strategy in course design, and 2) We develop a context-aware deep learning framework to draw insights from the student-generated materials for (i) Detecting anomalies in group activities and (ii) Predicting the median quiz performance of students in each group. This work opens up an avenue for effectively implementing a constructivism learning strategy in large-scale and online courses to build a sense of community between learners while providing an automated tool for instructors to identify at-risk groups.