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Transferring programming skills learned in the classroom to diverse real-world scenarios is both essential and challenging in computing education. This experience report describes an approach to facilitate learning transfer by fostering adaptive expertise. Students were engaged in co-creating contextualized worked-out examples, including step-by-step solutions. Through three homework assignments in a Spring 2023 database programming course, we observed substantial improvements, where students generated detailed and accurate solutions and enriched their problem-solving contexts from simple phrases to detailed stories, drawn from 17 real-life scenarios. Our results also suggest that the peer assessment process cultivated a supportive learning environment and fostered adaptive expertise. We discuss the lessons learned and draw pedagogical implications for integrating student-generated contextualized materials in other programming courses.