This research examines the ingenious activity, relationships, and power dynamics that mediate learning in the video game play of youth from non-dominant communities. Through extensive analyses of a multi-sited digital ethnography, the dissertation draws on data collected from a study on the everyday media practices of working-class families, as well as analyses of youth activity on a live-streaming platform called Twitch to analyze learning in playful contexts. The three-article dissertation highlights the importance of studying youth digital activities and phenomenon across media ecologies to understand how youth develop repertoires and dispositions. By drawing on a Cultural Historical Activity Theoretical (CHAT) framework, the three articles call attention to the generative possibilities of focusing on youth agency, ingenuity, and digital resistance to counter deficit approaches around the everyday media practices of youth. The first article of the dissertation examines how a Latino boy, Richard, draws on the relational expertise of a community of gamers to learn how to exploit glitches in the games he played. Specifically, the study shows how the focal child, learns to subvert video game system designs, and argues that by deviating from the norms of play, children from non-dominant communities, like Richard, can expand and transform the learning ecologies they participate in. The second article of the dissertation examines youth activity on a live-streaming platform, called Twitch, to analyze how race discourse mediates learning in gaming spaces. This article documents how youth engage, reproduce, and/or challenge race discourse that emerges in their digital play ecologies. Finally, the third article draws on “Learning by Observing and Pitching In” (LOPI) as an analytical frame to examine how children and adults in gaming communities work as a fluid ensemble to accomplish endeavors in their online activity. The article argues that online gaming spaces are organized in ways that support collaboration amongst adults and children and, as a result, can be leveraged to develop relational equity between adult educators and their students. Overall, the three-article dissertation study has implications for how we can design robust digital and hybrid learning ecologies that center play and youths' media interest-driven practices.