Within academic institutions, writing centers are uniquely situated, socially rich sites for exploring learning and literacy. I examine the work of the Michigan Tech Writing Center's UN 1002 World Cultures study teams primarily because student participants and Writing Center coaches are actively engaged in structuring their own learning and meaning-making processes. My research reveals that learning is closely linked to identity formation and leading the teams is an important component of the coaches' educational experiences. I argue that supporting this type of learning requires an expanded understanding of literacy and significant changes to how learning environments are conceptualized and developed. This ethnographic study draws on data collected from recordings and observations of one semester of team sessions, my own experiences as a team coach and UN 1002 teaching assistant, and interviews with Center coaches prior to their graduation. I argue that traditional forms of assessment and analysis emerging from individualized instruction models of learning cannot fully account for the dense configurations of social interactions identified in the Center's program. Instead, I view the Center as an open system and employ social theories of learning and literacy to uncover how the negotiation of meaning in one context influences and is influenced by structures and interactions within as well as beyond its boundaries. I focus on the program design, its enaction in practice, and how engagement in this type of writing center work influences coaches' learning trajectories. I conclude that, viewed as participation in a community of practice, the learning theory informing the program design supports identity formation--a key aspect of learning as argued by Etienne Wenger (1998). The findings of this study challenge misconceptions of peer learning both in writing centers and higher education that relegate peer tutoring to the role of support for individualized models of learning. Instead, this dissertation calls for consideration of new designs that incorporate peer learning as an integral component. Designing learning contexts that cultivate and support the formation of new identities is complex, involves a flexible and opportunistic design structure, and requires the availability of multiple forms of participation and connections across contexts. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]