The authors share two case studies that provide preliminary data for a National Science Foundation Innovative Technology Experiences for Students and Teachers award at the intersection of interactive media for STEM career development. The chapter explores the potential of culturally relevant Esports gaming activities to enhance students' motivation, attitudes, and awareness towards careers in the digital media aspects of traditional video gaming and Esports. Towards designing authentic learning environments, the findings from the two case studies revealed that play ecosystems help identify social, cultural, and historical attributes of gaming communities; students need opportunities to take on leadership roles in the design and development of the environment by trusting that they are capable of technological innovations; and that social and cultural nuance of tools, rules, and language define gaming communities.
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